Product Name

  • Name

    3-Hydroxy-2,4,5-trifluorobenzoic acid

  • EINECS
  • CAS No. 116751-24-7
  • Article Data7
  • CAS DataBase
  • Density 1.699 g/cm3
  • Solubility
  • Melting Point 144-145 °C
  • Formula C7H3F3O3
  • Boiling Point 292.6 °C at 760 mmHg
  • Molecular Weight 192.094
  • Flash Point 130.8 °C
  • Transport Information
  • Appearance white to light yellow-beige powder
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 116751-24-7 (3-Hydroxy-2,4,5-trifluorobenzoic acid)
  • Hazard Symbols IrritantXi
  • Synonyms 2,4,5-Trifluoro-3-hydroxybenzoic acid;2,4,5-Trifluoro-3-hydroxybenzoicacid;
  • PSA 57.53000
  • LogP 1.50770

Synthetic route

3,4,5,6-tetrafluorophthalic acid
652-03-9

3,4,5,6-tetrafluorophthalic acid

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: 3,4,5,6-tetrafluorophthalic acid With sodium hydroxide In water at 90℃; for 9h;
Stage #2: With hydrogenchloride; tri-n-propylamine In water at 140℃; under 7500.75 Torr; for 7h; pH=1; Temperature;		90.35%
3,4,6-trifluoro-5-hydroxyphthalic acid
28749-88-4

3,4,6-trifluoro-5-hydroxyphthalic acid

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
In water90%
In water90%
4-methoxy-3,5,6-trifluorophthalic acid
28889-41-0

4-methoxy-3,5,6-trifluorophthalic acid

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
In water74%
In water74%
2-bromo-3,4,6-trifluoro-5-hydroxy-benzoic acid

2-bromo-3,4,6-trifluoro-5-hydroxy-benzoic acid

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; zinc In water at 25℃; for 2h;1.92 g
triisopropyl(2,3,6-trifluorophenoxy)silane

triisopropyl(2,3,6-trifluorophenoxy)silane

carbon dioxide
124-38-9

carbon dioxide

A

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

B

2,3,5-trifluoro-4-hydroxybenzoic acid
156839-10-0

2,3,5-trifluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: triisopropyl(2,3,6-trifluorophenoxy)silane With 2,2,6,6-tetramethylpiperidinyl-lithium In diethyl ether
Stage #2: carbon dioxide In diethyl ether
Stage #3: With hydrogenchloride Title compound not separated from byproducts;
...Expand
carbon dioxide
124-38-9

carbon dioxide

1,2,4-trifluoro-3-(methoxymethoxy)benzene

1,2,4-trifluoro-3-(methoxymethoxy)benzene

A

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

B

2,3,5-trifluoro-4-hydroxybenzoic acid
156839-10-0

2,3,5-trifluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: 1,2,4-trifluoro-3-(methoxymethoxy)benzene With n-butyllithium In tetrahydrofuran
Stage #2: carbon dioxide In tetrahydrofuran; hexane
Stage #3: With hydrogenchloride In water Title compound not separated from byproducts;
Stage #1: 1,2,4-trifluoro-3-(methoxymethoxy)benzene With lithium diisopropyl amide In tetrahydrofuran
Stage #2: carbon dioxide In tetrahydrofuran
Stage #3: With hydrogenchloride In water Title compound not separated from byproducts;
...Expand
1-bromo-2,3,5-trifluoro-4-(methoxymethoxy)benzene
851341-31-6

1-bromo-2,3,5-trifluoro-4-(methoxymethoxy)benzene

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 2,2,6,6-tetramethylpiperidine; potassium tert-butoxide; N,N,N',N'',N''-pentamethylenediamine / butyllithium / tetrahydrofuran; hexane / 0.75 h / -125 °C
1.2: tetrahydrofuran; hexane
2.1: HCl / H2O
3.1: 1.92 g / NaOH; zinc powder / H2O / 2 h / 25 °C
View Scheme
2-bromo-3,4,6-trifluoro-5-methoxymethoxy-benzoic acid

2-bromo-3,4,6-trifluoro-5-methoxymethoxy-benzoic acid

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / H2O
2: 1.92 g / NaOH; zinc powder / H2O / 2 h / 25 °C
View Scheme
2,3,6-trifluorophenol
113798-74-6

2,3,6-trifluorophenol

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 82 percent / imidazole / dimethylformamide / 20 h / 25 °C
2.1: lithium 2,2,6,6-tetramethylpiperidide / diethyl ether
2.2: diethyl ether
2.3: hydrochloric acid
View Scheme
Multi-step reaction with 5 steps
1.1: 87 percent / N-bromosuccinimide / CHCl3 / 2 h / 0 °C
2.1: 88 percent / N-ethyldiisopropylamine / CH2Cl2 / 2 h / 25 °C
3.1: 2,2,6,6-tetramethylpiperidine; potassium tert-butoxide; N,N,N',N'',N''-pentamethylenediamine / butyllithium / tetrahydrofuran; hexane / 0.75 h / -125 °C
3.2: tetrahydrofuran; hexane
4.1: HCl / H2O
5.1: 1.92 g / NaOH; zinc powder / H2O / 2 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 87 percent / N-ethyldiisopropylamine / CH2Cl2 / 25 °C
2.1: lithium diisopropylamide / tetrahydrofuran
2.2: tetrahydrofuran
2.3: HCl / H2O
View Scheme
4-bromo-2,3,6-trifluorophenol
192446-70-1

4-bromo-2,3,6-trifluorophenol

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 88 percent / N-ethyldiisopropylamine / CH2Cl2 / 2 h / 25 °C
2.1: 2,2,6,6-tetramethylpiperidine; potassium tert-butoxide; N,N,N',N'',N''-pentamethylenediamine / butyllithium / tetrahydrofuran; hexane / 0.75 h / -125 °C
2.2: tetrahydrofuran; hexane
3.1: HCl / H2O
4.1: 1.92 g / NaOH; zinc powder / H2O / 2 h / 25 °C
View Scheme
N-methyl-tetrafluorophthalimide
33795-85-6

N-methyl-tetrafluorophthalimide

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: N-methyl-tetrafluorophthalimide With sodium hydroxide for 10h; Reflux;
Stage #2: With sulfuric acid at 70 - 105℃; for 8h; Temperature; Reagent/catalyst;
Multi-step reaction with 2 steps
1: sodium hydroxide; zinc(II) chloride / water / 8 h / 100 °C / Large scale
2: hydrogenchloride / Reflux
View Scheme
Multi-step reaction with 2 steps
1: water; zinc(II) chloride; sodium hydroxide / 8 h / 100 °C / Large scale
2: hydrogenchloride / water / Reflux
View Scheme
C8F3O5(3-)*3Na(1+)

C8F3O5(3-)*3Na(1+)

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
With hydrogenchloride Reflux;
With hydrogenchloride In water Reflux;
ethyl iodide
75-03-6

ethyl iodide

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

ethyl 3-ethoxy-2,4,5-trifluorobenzoate
172602-80-1

ethyl 3-ethoxy-2,4,5-trifluorobenzoate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 18h;92%
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

methyl iodide
74-88-4

methyl iodide

methyl 3-methoxy-2,4,5-trifluorobenzoate
136897-64-8

methyl 3-methoxy-2,4,5-trifluorobenzoate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 18h;91%
With sodium hydride In N,N-dimethyl-formamide
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl 3-methoxy-2,4,5-trifluorobenzoate
136897-64-8

methyl 3-methoxy-2,4,5-trifluorobenzoate

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester
137234-92-5

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl acetamide; water91%
...Expand
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3-methoxy-2,4,5-trifluorobenzoic acid
112811-65-1

3-methoxy-2,4,5-trifluorobenzoic acid

Conditions
ConditionsYield
With potassium dihydrogenphosphate; N-ethyl-N,N-diisopropylamine In water at 170℃; for 8h; Reagent/catalyst; Solvent; Temperature; Autoclave;85.2%
Stage #1: 2,4,5-trifluoro-3-hydroxybenzoic acid; carbonic acid dimethyl ester With sodium hydroxide at 55 - 60℃; for 2h; pH=8 - 10; Large scale;
Stage #2: With hydrogenchloride In water at 35℃; Large scale;		85%
methanol
67-56-1

methanol

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester
137234-92-5

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester

Conditions
ConditionsYield
sulfuric acid at 70℃; for 18h; Sealed tube; Heating / reflux;79%
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

methyl 3-methoxy-2,4,5-trifluorobenzoate
136897-64-8

methyl 3-methoxy-2,4,5-trifluorobenzoate

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester
137234-92-5

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With dmap; potassium iodide In water; carbonic acid dimethyl ester78%
2-(tert-butyldimethylsilyloxy)ethyl bromide
86864-60-0

2-(tert-butyldimethylsilyloxy)ethyl bromide

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl-3-[(2-{[(1,1-dimethylethyl)(dimethyl)siyl]oxy}ethyl)oxy]-2,4,5-trifluorobenzoate
838856-71-6

2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl-3-[(2-{[(1,1-dimethylethyl)(dimethyl)siyl]oxy}ethyl)oxy]-2,4,5-trifluorobenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 15h;23%
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

2,4,5-Trifluoro-3-hydroxy-benzoyl chloride
1042641-60-0

2,4,5-Trifluoro-3-hydroxy-benzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

3-ethoxy-2,4,5-trifluorobenzoyl chloride
172602-81-2

3-ethoxy-2,4,5-trifluorobenzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

3-ethoxy-2,4,5-trifluorobenzoic acid
169507-61-3

3-ethoxy-2,4,5-trifluorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

ethyl (3-ethoxy-2,4,5-trifluorobenzoyl)acetate
172602-82-3

ethyl (3-ethoxy-2,4,5-trifluorobenzoyl)acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

(Z)-3-Ethoxy-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester

(Z)-3-Ethoxy-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

(Z)-3-Cyclopropylamino-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester
1027303-55-4

(Z)-3-Cyclopropylamino-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylic acid
172602-86-7

5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
9: 89 percent / H2 / Raney nickel / tetrahydrofuran / 4 h / 24 - 30 °C / 1241.2 - 1551.4 Torr
10: 90 percent / 1.0 N aq. NaOH / ethanol / 18 h / Ambient temperature
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate
172602-83-4

ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate
172602-85-6

ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
9: 89 percent / H2 / Raney nickel / tetrahydrofuran / 4 h / 24 - 30 °C / 1241.2 - 1551.4 Torr
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-5-nitro-4-oxo-3-quinolinecarboxylate
172602-84-5

ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-5-nitro-4-oxo-3-quinolinecarboxylate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

5-Amino-7-(3-amino-piperidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

5-Amino-7-(3-amino-piperidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
9: 89 percent / H2 / Raney nickel / tetrahydrofuran / 4 h / 24 - 30 °C / 1241.2 - 1551.4 Torr
10: 90 percent / 1.0 N aq. NaOH / ethanol / 18 h / Ambient temperature
11: 1.) Et3N, 2.) TFA / 1.) DMSO, CH3CN, RT, 18 h, 2.) CH2Cl2, from 0 deg C to RT, 1 h
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

5-Amino-7-(3-amino-pyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

5-Amino-7-(3-amino-pyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
9: 89 percent / H2 / Raney nickel / tetrahydrofuran / 4 h / 24 - 30 °C / 1241.2 - 1551.4 Torr
10: 90 percent / 1.0 N aq. NaOH / ethanol / 18 h / Ambient temperature
11: 1.) Et3N, 2.) TFA / 1.) DMSO, CH3CN, RT, 18 h, 2.) CH2Cl2, from 0 deg C to RT, 1 h
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

5-Amino-7-(3-aminomethyl-3-methyl-pyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

5-Amino-7-(3-aminomethyl-3-methyl-pyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
9: 89 percent / H2 / Raney nickel / tetrahydrofuran / 4 h / 24 - 30 °C / 1241.2 - 1551.4 Torr
10: 90 percent / 1.0 N aq. NaOH / ethanol / 18 h / Ambient temperature
11: 1.) Et3N, 2.) TFA / 1.) DMSO, CH3CN, RT, 18 h, 2.) CH2Cl2, from 0 deg C to RT, 1 h
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