Product Name

  • Name

    3-CYANO-4-ISOPROPOXYBENZOIC ACID

  • EINECS
  • CAS No. 258273-31-3
  • Article Data11
  • CAS DataBase
  • Density 1.231 g/cm3
  • Solubility
  • Melting Point
  • Formula C11H11NO3
  • Boiling Point 371.39 °C at 760 mmHg
  • Molecular Weight 205.213
  • Flash Point 178.41 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 258273-31-3 (3-CYANO-4-ISOPROPOXYBENZOIC ACID)
  • Hazard Symbols
  • Synonyms 3-Cyano-4-[(1-methylethyl)oxy]benzoicacid;3-Cyano-4-isopropoxybenzoic acid;3-Cyano-4-isopropyloxybenzoic acid;
  • PSA 70.32000
  • LogP 2.04368

Synthetic route

3-cyano-4-isopropoxybenzoic acid methyl ester
213598-11-9

3-cyano-4-isopropoxybenzoic acid methyl ester

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Stage #1: methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate With ethanol; sodium hydroxide In tetrahydrofuran at 20℃; for 4h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water		92%
With ethanol; sodium hydroxide In tetrahydrofuran at 20℃; for 4h;92%
Stage #1: methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate With potassium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 16h;
Stage #2: With hydrogenchloride In water for 2h;		87%
3-bromo-4-hydroxy-benzoic acid
14348-41-5

3-bromo-4-hydroxy-benzoic acid

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C
2.1: 1-methyl-pyrrolidin-2-one / 16 h / 200 °C
3.1: water; lithium hydroxide / 1,4-dioxane / 1.5 h / 30 °C
3.2: 20 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride / 20 °C
2: potassium carbonate / acetonitrile / Reflux
3: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
4: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride / water / 20 °C
2.1: potassium carbonate / acetonitrile / Reflux
3.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
4.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
4.2: pH 4 - 5
View Scheme
1-methylethyl 3-bromo-4-[(1-methylethyl)oxy]benzoate
1034689-05-8

1-methylethyl 3-bromo-4-[(1-methylethyl)oxy]benzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1-methyl-pyrrolidin-2-one / 16 h / 200 °C
2.1: water; lithium hydroxide / 1,4-dioxane / 1.5 h / 30 °C
2.2: 20 °C
View Scheme
1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate
1261173-10-7

1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Stage #1: 1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate With water; lithium hydroxide In 1,4-dioxane at 30℃; for 1.5h;
Stage #2: With hydrogenchloride In 1,4-dioxane; water at 20℃;
Stage #1: 1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate With water; sodium hydroxide In isopropyl alcohol at 20℃;
Stage #2: With hydrogenchloride In water pH=~ 2;
Stage #1: 1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate With water; sodium hydroxide In isopropyl alcohol at 20℃;
Stage #2: With hydrogenchloride In water pH=2;
methyl 3-iodo-4-hydroxybenzoate
15126-06-4

methyl 3-iodo-4-hydroxybenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium cyanide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere
3: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: copper(l) cyanide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
1.2: 12 h / 90 °C / Cooling with ice
2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
2.2: pH 4 - 5
View Scheme
Multi-step reaction with 3 steps
1: sodium cyanide / N,N-dimethyl-formamide / 18 h / 105 °C
2: potassium carbonate / N,N-dimethyl-formamide / 14 h / 90 °C
3: sodium hydroxide; ethanol / tetrahydrofuran / 4 h / 20 °C
View Scheme
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Iodine monochloride; acetic acid / 20 - 65 °C
2: sodium cyanide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere
4: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: Iodine monochloride / acetic acid / 65 °C
2.1: copper(l) cyanide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
2.2: 12 h / 90 °C / Cooling with ice
3.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
3.2: pH 4 - 5
View Scheme
Multi-step reaction with 4 steps
1: acetic acid; Iodine monochloride / 24.6 h / 20 - 65 °C
2: sodium cyanide / N,N-dimethyl-formamide / 18 h / 105 °C
3: potassium carbonate / N,N-dimethyl-formamide / 14 h / 90 °C
4: sodium hydroxide; ethanol / tetrahydrofuran / 4 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: magnesium chloride / dichloromethane / 44 °C / Large scale
2: hydroxylamine hydrochloride; acetyl chloride / N,N-dimethyl-formamide; acetonitrile / 2 h / 80 °C / Large scale
3: potassium carbonate / N,N-dimethyl-formamide; acetonitrile / 80 °C / Large scale
4: sodium hydroxide / tetrahydrofuran / 1 h / 60 °C / Large scale
View Scheme
methyl 3-cyano-4-hydroxybenzoate
156001-68-2

methyl 3-cyano-4-hydroxybenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere
2: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 80 °C
2: sodium hydroxide / methanol; water / 2 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 90 °C
2: sodium hydroxide; ethanol / tetrahydrofuran / 4 h / 20 °C
View Scheme
methyl 3-bromo-4-hydroxybenzoate
29415-97-2

methyl 3-bromo-4-hydroxybenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetonitrile / Reflux
2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
3: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetonitrile / Reflux
2.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
3.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
3.2: pH 4 - 5
View Scheme
Multi-step reaction with 3 steps
1: copper(l) iodide / N,N-dimethyl-formamide / 120 °C
2: potassium carbonate / N,N-dimethyl-formamide / 80 °C
3: sodium hydroxide / methanol; water / 2 h / 25 °C
View Scheme
3-cyano-4-fluorobenzoic acid methyl ester
676602-31-6

3-cyano-4-fluorobenzoic acid methyl ester

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 20 °C / Cooling with ice
1.2: 16 h / 50 °C
2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
2.2: pH ~ 2
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 17 h / 20 - 50 °C / Cooling with ice
2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
2.2: pH 2
View Scheme
3-cyano-4-fluorobenzoic acid
171050-06-9

3-cyano-4-fluorobenzoic acid

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / 80 - 90 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 20 °C / Cooling with ice
2.2: 16 h / 50 °C
3.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
3.2: pH ~ 2
View Scheme
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / 90 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 17 h / 20 - 50 °C / Cooling with ice
3.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
3.2: pH 2
View Scheme
methyl 3-bromo-4-isopropoxybenzoate
213598-10-8

methyl 3-bromo-4-isopropoxybenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
2: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
2.2: pH 4 - 5
View Scheme
methyl 3-formyl-4-hydroxybenzoate
24589-99-9

methyl 3-formyl-4-hydroxybenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydroxylamine hydrochloride; acetyl chloride / N,N-dimethyl-formamide; acetonitrile / 2 h / 80 °C / Large scale
2: potassium carbonate / N,N-dimethyl-formamide; acetonitrile / 80 °C / Large scale
3: sodium hydroxide / tetrahydrofuran / 1 h / 60 °C / Large scale
View Scheme
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

3-cyano-4-[(1-methylethyl)oxy]benzoyl chloride
1072948-37-8

3-cyano-4-[(1-methylethyl)oxy]benzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;100%
With oxalyl dichloride; N,N-dimethyl-formamide at 20℃; for 4h; Product distribution / selectivity;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 4h;100%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

methanol
67-56-1

methanol

3-cyano-4-isopropoxybenzoic acid methyl ester
213598-11-9

3-cyano-4-isopropoxybenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid; methanol With diazomethyl-trimethyl-silane In dichloromethane at 0 - 20℃; for 1.8h;
Stage #2: With acetic acid In dichloromethane at 20℃;		100%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

thiosemicarbazide
79-19-6

thiosemicarbazide

5-(5-amino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile
1258440-55-9

5-(5-amino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile

Conditions
ConditionsYield
With trichlorophosphate at 90℃; for 3h;99%
Stage #1: 3-cyano-4-isopropoxybenzoic acid; thiosemicarbazide With trichlorophosphate at 90℃; for 3h;
Stage #2: With sodium hydroxide In water at 35℃; pH=10; Cooling with ice;		99%
Stage #1: 3-cyano-4-isopropoxybenzoic acid; thiosemicarbazide With trichlorophosphate at 90℃; for 3h;
Stage #2: With sodium hydroxide at 35℃; pH=10; Cooling with ice;		99%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

1,1-dimethylethyl 8-[(hydroxyamino)(imino)methyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
1167416-24-1

1,1-dimethylethyl 8-[(hydroxyamino)(imino)methyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

1,1-dimethylethyl 8-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
1167416-65-0

1,1-dimethylethyl 8-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Heating;92%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide

3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide

N-((3 -cyano-4-isopropoxybenzoyl)oxy)-3 -ethoxy-1H-indene-7-carboximidamide

N-((3 -cyano-4-isopropoxybenzoyl)oxy)-3 -ethoxy-1H-indene-7-carboximidamide

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide In N,N-dimethyl-formamide for 0.583333h;		90%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In water; N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide In water; N,N-dimethyl-formamide for 0.583333h;		90%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide In N,N-dimethyl-formamide for 0.583333h;		90%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide

3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide

N-((3-cyano-4-isopropoxybenzoyl)oxy)-3-ethoxy-1H-indene-7-carboximidamide

N-((3-cyano-4-isopropoxybenzoyl)oxy)-3-ethoxy-1H-indene-7-carboximidamide

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide In N,N-dimethyl-formamide for 0.583333h;		90%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide In N,N-dimethyl-formamide at 20℃; for 0.583333h;		90%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

tert-butyl 3-(N'-hydroxycarbamimidoyl)-4-methyl-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate
1333996-58-9

tert-butyl 3-(N'-hydroxycarbamimidoyl)-4-methyl-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate

tert-butyl 3-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-4-methyl-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate
1333996-60-3

tert-butyl 3-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-4-methyl-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: tert-butyl 3-(N'-hydroxycarbamimidoyl)-4-methyl-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate In N,N-dimethyl-formamide at 20 - 100℃; for 17.5h;		88%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

2-chloro-4-(1,3-dioxolan-2-yl)-N′-hydroxybenzimidamide

2-chloro-4-(1,3-dioxolan-2-yl)-N′-hydroxybenzimidamide

5-(3-(2-chloro-4-(1,3-dioxolan-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

5-(3-(2-chloro-4-(1,3-dioxolan-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid; 2-chloro-4-(1,3-dioxolan-2-yl)-N′-hydroxybenzimidamide With potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: With benzotriazol-1-ol In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere;		87%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 2-chloro-4-(1,3-dioxolan-2-yl)-N′-hydroxybenzimidamide In N,N-dimethyl-formamide at 110℃; for 4h; Inert atmosphere;		87%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

4-(1,3-dioxolan-2-yl)-2-fluoro-N′-hydroxybenzimidamide

4-(1,3-dioxolan-2-yl)-2-fluoro-N′-hydroxybenzimidamide

5-(3-(4-(1,3-dioxolan-2-yl)-2-fluorophenyl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

5-(3-(4-(1,3-dioxolan-2-yl)-2-fluorophenyl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid; 4-(1,3-dioxolan-2-yl)-2-fluoro-N′-hydroxybenzimidamide With potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: With benzotriazol-1-ol In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere;		81.7%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 4-(1,3-dioxolan-2-yl)-2-fluoro-N′-hydroxybenzimidamide In N,N-dimethyl-formamide at 110℃; for 4h; Inert atmosphere;		81.7%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

N-{(1S)-1-[(4-bromophenyl)methyl]-3-hydroxypropyl}-3-cyano-4-[(1-methylethyl)oxy]benzamide

N-{(1S)-1-[(4-bromophenyl)methyl]-3-hydroxypropyl}-3-cyano-4-[(1-methylethyl)oxy]benzamide

Conditions
ConditionsYield
Stage #1: (3S)-3-amino-4-(4-bromophenyl)-1-butanol hydrochloride With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) for 0.05h;
Stage #2: 3-cyano-4-isopropoxybenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In DMF (N,N-dimethyl-formamide) at 20℃; for 1.5h;
Stage #3: With water In DMF (N,N-dimethyl-formamide)		78%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

N-hydroxybenzofuran-5-carboximidamide
1307231-09-9

N-hydroxybenzofuran-5-carboximidamide

5-(3-(benzofuran-5-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile
1307230-52-9

5-(3-(benzofuran-5-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: N-hydroxybenzofuran-5-carboximidamide In N,N-dimethyl-formamide at 20 - 85℃;		69%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

(S)-1-azido-N’-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide

(S)-1-azido-N’-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide

(S)-5-(3-(1-azido-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

(S)-5-(3-(1-azido-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: (S)-1-azido-N’-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide In N,N-dimethyl-formamide at 115℃; for 24h; Reagent/catalyst; Solvent;		69%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

tert-butyl (1S)-4-[(E)-N’-hydroxycarbamimidoyl]-2,3-dihydro-1H-inden-1-yl N-[2-[(tert-butyldimethylsilyl)oxy]ethyl]carbamate

tert-butyl (1S)-4-[(E)-N’-hydroxycarbamimidoyl]-2,3-dihydro-1H-inden-1-yl N-[2-[(tert-butyldimethylsilyl)oxy]ethyl]carbamate

tert-butyl(1S)-4-[5-[3-cyano-4-(propan-2-yloxy)phenyl]-1,2,4-oxadiazol-3-yl]-2,3-dihydro-1H-inden-1-yl-N-[2-[(tert-butyldimethylsilyl)oxy]ethyl]carbamate

tert-butyl(1S)-4-[5-[3-cyano-4-(propan-2-yloxy)phenyl]-1,2,4-oxadiazol-3-yl]-2,3-dihydro-1H-inden-1-yl-N-[2-[(tert-butyldimethylsilyl)oxy]ethyl]carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1,2-dichloro-ethane In N,N-dimethyl-formamide at 20 - 85℃; for 1.5h;67%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

(1S)-1-({2-[(tert-butyldimethylsilyl)oxy]ethyl}[(S)-2-methylpropane-2-sulfinyl]amino)-N-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide

(1S)-1-({2-[(tert-butyldimethylsilyl)oxy]ethyl}[(S)-2-methylpropane-2-sulfinyl]amino)-N-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide

5-{3-[(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl}-2-(propan-2-yloxy)benzonitrile hydrochloride

5-{3-[(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl}-2-(propan-2-yloxy)benzonitrile hydrochloride

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid; (1S)-1-({2-[(tert-butyldimethylsilyl)oxy]ethyl}[(S)-2-methylpropane-2-sulfinyl]amino)-N-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In toluene at 20 - 90℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 0 - 90℃; for 1h; Solvent;		63.6%
3-cyano-4-isopropoxybenzoic acid methyl ester
213598-11-9

3-cyano-4-isopropoxybenzoic acid methyl ester

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Stage #1: methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate With ethanol; sodium hydroxide In tetrahydrofuran at 20℃; for 4h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water		92%
With ethanol; sodium hydroxide In tetrahydrofuran at 20℃; for 4h;92%
Stage #1: methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate With potassium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 16h;
Stage #2: With hydrogenchloride In water for 2h;		87%
3-bromo-4-hydroxy-benzoic acid
14348-41-5

3-bromo-4-hydroxy-benzoic acid

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C
2.1: 1-methyl-pyrrolidin-2-one / 16 h / 200 °C
3.1: water; lithium hydroxide / 1,4-dioxane / 1.5 h / 30 °C
3.2: 20 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride / 20 °C
2: potassium carbonate / acetonitrile / Reflux
3: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
4: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride / water / 20 °C
2.1: potassium carbonate / acetonitrile / Reflux
3.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
4.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
4.2: pH 4 - 5
View Scheme
1-methylethyl 3-bromo-4-[(1-methylethyl)oxy]benzoate
1034689-05-8

1-methylethyl 3-bromo-4-[(1-methylethyl)oxy]benzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1-methyl-pyrrolidin-2-one / 16 h / 200 °C
2.1: water; lithium hydroxide / 1,4-dioxane / 1.5 h / 30 °C
2.2: 20 °C
View Scheme
1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate
1261173-10-7

1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Stage #1: 1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate With water; lithium hydroxide In 1,4-dioxane at 30℃; for 1.5h;
Stage #2: With hydrogenchloride In 1,4-dioxane; water at 20℃;
Stage #1: 1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate With water; sodium hydroxide In isopropyl alcohol at 20℃;
Stage #2: With hydrogenchloride In water pH=~ 2;
Stage #1: 1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate With water; sodium hydroxide In isopropyl alcohol at 20℃;
Stage #2: With hydrogenchloride In water pH=2;
methyl 3-iodo-4-hydroxybenzoate
15126-06-4

methyl 3-iodo-4-hydroxybenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium cyanide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere
3: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: copper(l) cyanide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
1.2: 12 h / 90 °C / Cooling with ice
2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
2.2: pH 4 - 5
View Scheme
Multi-step reaction with 3 steps
1: sodium cyanide / N,N-dimethyl-formamide / 18 h / 105 °C
2: potassium carbonate / N,N-dimethyl-formamide / 14 h / 90 °C
3: sodium hydroxide; ethanol / tetrahydrofuran / 4 h / 20 °C
View Scheme
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Iodine monochloride; acetic acid / 20 - 65 °C
2: sodium cyanide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere
4: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: Iodine monochloride / acetic acid / 65 °C
2.1: copper(l) cyanide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
2.2: 12 h / 90 °C / Cooling with ice
3.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
3.2: pH 4 - 5
View Scheme
Multi-step reaction with 4 steps
1: acetic acid; Iodine monochloride / 24.6 h / 20 - 65 °C
2: sodium cyanide / N,N-dimethyl-formamide / 18 h / 105 °C
3: potassium carbonate / N,N-dimethyl-formamide / 14 h / 90 °C
4: sodium hydroxide; ethanol / tetrahydrofuran / 4 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: magnesium chloride / dichloromethane / 44 °C / Large scale
2: hydroxylamine hydrochloride; acetyl chloride / N,N-dimethyl-formamide; acetonitrile / 2 h / 80 °C / Large scale
3: potassium carbonate / N,N-dimethyl-formamide; acetonitrile / 80 °C / Large scale
4: sodium hydroxide / tetrahydrofuran / 1 h / 60 °C / Large scale
View Scheme
methyl 3-cyano-4-hydroxybenzoate
156001-68-2

methyl 3-cyano-4-hydroxybenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere
2: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 80 °C
2: sodium hydroxide / methanol; water / 2 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 90 °C
2: sodium hydroxide; ethanol / tetrahydrofuran / 4 h / 20 °C
View Scheme
methyl 3-bromo-4-hydroxybenzoate
29415-97-2

methyl 3-bromo-4-hydroxybenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetonitrile / Reflux
2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
3: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetonitrile / Reflux
2.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
3.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
3.2: pH 4 - 5
View Scheme
Multi-step reaction with 3 steps
1: copper(l) iodide / N,N-dimethyl-formamide / 120 °C
2: potassium carbonate / N,N-dimethyl-formamide / 80 °C
3: sodium hydroxide / methanol; water / 2 h / 25 °C
View Scheme
3-cyano-4-fluorobenzoic acid methyl ester
676602-31-6

3-cyano-4-fluorobenzoic acid methyl ester

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 20 °C / Cooling with ice
1.2: 16 h / 50 °C
2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
2.2: pH ~ 2
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 17 h / 20 - 50 °C / Cooling with ice
2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
2.2: pH 2
View Scheme
3-cyano-4-fluorobenzoic acid
171050-06-9

3-cyano-4-fluorobenzoic acid

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / 80 - 90 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 20 °C / Cooling with ice
2.2: 16 h / 50 °C
3.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
3.2: pH ~ 2
View Scheme
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / 90 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 17 h / 20 - 50 °C / Cooling with ice
3.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
3.2: pH 2
View Scheme
methyl 3-bromo-4-isopropoxybenzoate
213598-10-8

methyl 3-bromo-4-isopropoxybenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
2: sodium hydroxide / methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
2.1: sodium hydroxide; water / isopropyl alcohol / 20 °C
2.2: pH 4 - 5
View Scheme
methyl 3-formyl-4-hydroxybenzoate
24589-99-9

methyl 3-formyl-4-hydroxybenzoate

3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydroxylamine hydrochloride; acetyl chloride / N,N-dimethyl-formamide; acetonitrile / 2 h / 80 °C / Large scale
2: potassium carbonate / N,N-dimethyl-formamide; acetonitrile / 80 °C / Large scale
3: sodium hydroxide / tetrahydrofuran / 1 h / 60 °C / Large scale
View Scheme
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

3-cyano-4-[(1-methylethyl)oxy]benzoyl chloride
1072948-37-8

3-cyano-4-[(1-methylethyl)oxy]benzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;100%
With oxalyl dichloride; N,N-dimethyl-formamide at 20℃; for 4h; Product distribution / selectivity;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 4h;100%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

methanol
67-56-1

methanol

3-cyano-4-isopropoxybenzoic acid methyl ester
213598-11-9

3-cyano-4-isopropoxybenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid; methanol With diazomethyl-trimethyl-silane In dichloromethane at 0 - 20℃; for 1.8h;
Stage #2: With acetic acid In dichloromethane at 20℃;		100%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

thiosemicarbazide
79-19-6

thiosemicarbazide

5-(5-amino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile
1258440-55-9

5-(5-amino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile

Conditions
ConditionsYield
With trichlorophosphate at 90℃; for 3h;99%
Stage #1: 3-cyano-4-isopropoxybenzoic acid; thiosemicarbazide With trichlorophosphate at 90℃; for 3h;
Stage #2: With sodium hydroxide In water at 35℃; pH=10; Cooling with ice;		99%
Stage #1: 3-cyano-4-isopropoxybenzoic acid; thiosemicarbazide With trichlorophosphate at 90℃; for 3h;
Stage #2: With sodium hydroxide at 35℃; pH=10; Cooling with ice;		99%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

1,1-dimethylethyl 8-[(hydroxyamino)(imino)methyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
1167416-24-1

1,1-dimethylethyl 8-[(hydroxyamino)(imino)methyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

1,1-dimethylethyl 8-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
1167416-65-0

1,1-dimethylethyl 8-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Heating;92%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide

3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide

N-((3 -cyano-4-isopropoxybenzoyl)oxy)-3 -ethoxy-1H-indene-7-carboximidamide

N-((3 -cyano-4-isopropoxybenzoyl)oxy)-3 -ethoxy-1H-indene-7-carboximidamide

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide In N,N-dimethyl-formamide for 0.583333h;		90%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In water; N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide In water; N,N-dimethyl-formamide for 0.583333h;		90%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide In N,N-dimethyl-formamide for 0.583333h;		90%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide

3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide

N-((3-cyano-4-isopropoxybenzoyl)oxy)-3-ethoxy-1H-indene-7-carboximidamide

N-((3-cyano-4-isopropoxybenzoyl)oxy)-3-ethoxy-1H-indene-7-carboximidamide

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide In N,N-dimethyl-formamide for 0.583333h;		90%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-ethoxy-N-hydroxy-1H-indene-7-carboximidamide In N,N-dimethyl-formamide at 20℃; for 0.583333h;		90%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

tert-butyl 3-(N'-hydroxycarbamimidoyl)-4-methyl-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate
1333996-58-9

tert-butyl 3-(N'-hydroxycarbamimidoyl)-4-methyl-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate

tert-butyl 3-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-4-methyl-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate
1333996-60-3

tert-butyl 3-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-4-methyl-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: tert-butyl 3-(N'-hydroxycarbamimidoyl)-4-methyl-5,6-dihydro-1,7-naphthyridine-7(8H)-carboxylate In N,N-dimethyl-formamide at 20 - 100℃; for 17.5h;		88%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

2-chloro-4-(1,3-dioxolan-2-yl)-N′-hydroxybenzimidamide

2-chloro-4-(1,3-dioxolan-2-yl)-N′-hydroxybenzimidamide

5-(3-(2-chloro-4-(1,3-dioxolan-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

5-(3-(2-chloro-4-(1,3-dioxolan-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid; 2-chloro-4-(1,3-dioxolan-2-yl)-N′-hydroxybenzimidamide With potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: With benzotriazol-1-ol In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere;		87%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 2-chloro-4-(1,3-dioxolan-2-yl)-N′-hydroxybenzimidamide In N,N-dimethyl-formamide at 110℃; for 4h; Inert atmosphere;		87%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

4-(1,3-dioxolan-2-yl)-2-fluoro-N′-hydroxybenzimidamide

4-(1,3-dioxolan-2-yl)-2-fluoro-N′-hydroxybenzimidamide

5-(3-(4-(1,3-dioxolan-2-yl)-2-fluorophenyl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

5-(3-(4-(1,3-dioxolan-2-yl)-2-fluorophenyl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid; 4-(1,3-dioxolan-2-yl)-2-fluoro-N′-hydroxybenzimidamide With potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: With benzotriazol-1-ol In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere;		81.7%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 4-(1,3-dioxolan-2-yl)-2-fluoro-N′-hydroxybenzimidamide In N,N-dimethyl-formamide at 110℃; for 4h; Inert atmosphere;		81.7%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

N-{(1S)-1-[(4-bromophenyl)methyl]-3-hydroxypropyl}-3-cyano-4-[(1-methylethyl)oxy]benzamide

N-{(1S)-1-[(4-bromophenyl)methyl]-3-hydroxypropyl}-3-cyano-4-[(1-methylethyl)oxy]benzamide

Conditions
ConditionsYield
Stage #1: (3S)-3-amino-4-(4-bromophenyl)-1-butanol hydrochloride With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) for 0.05h;
Stage #2: 3-cyano-4-isopropoxybenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In DMF (N,N-dimethyl-formamide) at 20℃; for 1.5h;
Stage #3: With water In DMF (N,N-dimethyl-formamide)		78%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

N-hydroxybenzofuran-5-carboximidamide
1307231-09-9

N-hydroxybenzofuran-5-carboximidamide

5-(3-(benzofuran-5-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile
1307230-52-9

5-(3-(benzofuran-5-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: N-hydroxybenzofuran-5-carboximidamide In N,N-dimethyl-formamide at 20 - 85℃;		69%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

(S)-1-azido-N’-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide

(S)-1-azido-N’-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide

(S)-5-(3-(1-azido-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

(S)-5-(3-(1-azido-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: (S)-1-azido-N’-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide In N,N-dimethyl-formamide at 115℃; for 24h; Reagent/catalyst; Solvent;		69%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

tert-butyl (1S)-4-[(E)-N’-hydroxycarbamimidoyl]-2,3-dihydro-1H-inden-1-yl N-[2-[(tert-butyldimethylsilyl)oxy]ethyl]carbamate

tert-butyl (1S)-4-[(E)-N’-hydroxycarbamimidoyl]-2,3-dihydro-1H-inden-1-yl N-[2-[(tert-butyldimethylsilyl)oxy]ethyl]carbamate

tert-butyl(1S)-4-[5-[3-cyano-4-(propan-2-yloxy)phenyl]-1,2,4-oxadiazol-3-yl]-2,3-dihydro-1H-inden-1-yl-N-[2-[(tert-butyldimethylsilyl)oxy]ethyl]carbamate

tert-butyl(1S)-4-[5-[3-cyano-4-(propan-2-yloxy)phenyl]-1,2,4-oxadiazol-3-yl]-2,3-dihydro-1H-inden-1-yl-N-[2-[(tert-butyldimethylsilyl)oxy]ethyl]carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1,2-dichloro-ethane In N,N-dimethyl-formamide at 20 - 85℃; for 1.5h;67%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

(1S)-1-({2-[(tert-butyldimethylsilyl)oxy]ethyl}[(S)-2-methylpropane-2-sulfinyl]amino)-N-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide

(1S)-1-({2-[(tert-butyldimethylsilyl)oxy]ethyl}[(S)-2-methylpropane-2-sulfinyl]amino)-N-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide

5-{3-[(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl}-2-(propan-2-yloxy)benzonitrile hydrochloride

5-{3-[(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl}-2-(propan-2-yloxy)benzonitrile hydrochloride

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid; (1S)-1-({2-[(tert-butyldimethylsilyl)oxy]ethyl}[(S)-2-methylpropane-2-sulfinyl]amino)-N-hydroxy-2,3-dihydro-1H-indene-4-carboximidamide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In toluene at 20 - 90℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 0 - 90℃; for 1h; Solvent;		63.6%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

4-(1,3-dioxolan-2-yl)-N1-hydroxybenzenecarboximidamide
852691-00-0

4-(1,3-dioxolan-2-yl)-N1-hydroxybenzenecarboximidamide

5-(3-(4-(1,3-dioxolan-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

5-(3-(4-(1,3-dioxolan-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid; 4-(1,3-dioxolan-2-yl)-N1-hydroxybenzenecarboximidamide With potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: With benzotriazol-1-ol In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere;		59.7%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 4-(1,3-dioxolan-2-yl)-N1-hydroxybenzenecarboximidamide In N,N-dimethyl-formamide at 110℃; for 4h; Inert atmosphere;		59.7%
With potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;53.1%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

tert-butyl 5-(N-hydroxycarbamimidoyl)-1H-indole-1-carboxylate
1233500-95-2

tert-butyl 5-(N-hydroxycarbamimidoyl)-1H-indole-1-carboxylate

tert-butyl 5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-1H-indole-1-carboxylate
1307231-08-8

tert-butyl 5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-1H-indole-1-carboxylate

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 1.5h; Inert atmosphere;
Stage #2: tert-butyl 5-(N-hydroxycarbamimidoyl)-1H-indole-1-carboxylate In N,N-dimethyl-formamide at 20℃; for 1h;		59%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

1,1-dimethylethyl 7-[(hydroxyamino)(imino)methyl]-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carboxylate
1167415-97-5

1,1-dimethylethyl 7-[(hydroxyamino)(imino)methyl]-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carboxylate

1,1-dimethylethyl 7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carboxylate
1167416-00-3

1,1-dimethylethyl 7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carboxylate

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: 1,1-dimethylethyl 7-[(hydroxyamino)(imino)methyl]-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carboxylate In N,N-dimethyl-formamide at 20 - 90℃; for 21h;		46%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20 - 90℃;
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

N-hydroxy-3-methylisonicotinimidamide

N-hydroxy-3-methylisonicotinimidamide

N-(3-cyano-4-isopropoxybenzoyloxy)-3-methylisonicotinimidamide
1307231-29-3

N-(3-cyano-4-isopropoxybenzoyloxy)-3-methylisonicotinimidamide

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: N-hydroxy-3-methylisonicotinimidamide In N,N-dimethyl-formamide		45%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

(R)-N,5-dihydroxy-5,6,7,8-tetrahydronaphthalene-1-carboximidamide
1307230-79-0

(R)-N,5-dihydroxy-5,6,7,8-tetrahydronaphthalene-1-carboximidamide

(R)-5-(3-(5-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile
1307230-03-0

(R)-5-(3-(5-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h;
Stage #2: (R)-N,5-dihydroxy-5,6,7,8-tetrahydronaphthalene-1-carboximidamide In N,N-dimethyl-formamide at 20 - 90℃; for 16h;		42.4%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

(S)-N,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide

(S)-N,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide

(S)-5-(3-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

(S)-5-(3-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;
Stage #2: (S)-N,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide In N,N-dimethyl-formamide at 20 - 85℃; for 20h;		40%
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

1,1-dimethylethyl 5-hydroxyamino(imino)methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate
1165923-57-8

1,1-dimethylethyl 5-hydroxyamino(imino)methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

1,1-dimethylethyl 5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate
1165923-65-8

1,1-dimethylethyl 5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Conditions
ConditionsYield
Stage #1: 3-cyano-4-isopropoxybenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1.5h;
Stage #2: 1,1-dimethylethyl 5-hydroxyamino(imino)methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 95℃; for 19h;		37%
Stage #1: 3-cyano-4-isopropoxybenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1.5h;
Stage #2: 1,1-dimethylethyl 5-hydroxyamino(imino)methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 95℃; for 19h;
3-cyano-4-isopropoxybenzoic acid
258273-31-3

3-cyano-4-isopropoxybenzoic acid

1,1-dimethylethyl 7-[(hydroxyamino)(imino)methyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
1167416-58-1

1,1-dimethylethyl 7-[(hydroxyamino)(imino)methyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

1,1-dimethylethyl 7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
1167416-59-2

1,1-dimethylethyl 7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20 - 120℃; for 36h;31%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20 - 120℃;

3-Cyano-4-isopropoxybenzoic acid Specification

The 3-Cyano-4-isopropoxybenzoic acid with the CAS number 258273-31-3 is also called Benzoic acid,3-cyano-4-(1-methylethoxy)-. The IUPAC name is 3-cyano-4-propan-2-yloxybenzoic acid. Its molecular formula is C11H11NO3. This chemical is a kind of organics. It should be stored in dry and cool environment.

The properties of the 3-Cyano-4-isopropoxybenzoic acid are: (1)ACD/LogP: 3.03; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 0; (5)ACD/BCF (pH 5.5): 5; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 41; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 70.32 Å2; (13)Index of Refraction: 1.551; (14)Molar Refractivity: 53.199 cm3; (15)Molar Volume: 166.751 cm3; (16)Polarizability: 21.09×10-24cm3; (17)Surface Tension: 53.133 dyne/cm; (18)Enthalpy of Vaporization: 65.24 kJ/mol; (19)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)Oc1ccc(cc1C#N)C(=O)O
(2)InChI: InChI=1/C11H11NO3/c1-7(2)15-10-4-3-8(11(13)14)5-9(10)6-12/h3-5,7H,1-2H3,(H,13,14)
(3)InChIKey: FQGLEMDXDTZJMJ-UHFFFAOYAU

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