Product Name

  • Name

    4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol

  • EINECS 1806241-263-5
  • CAS No. 184475-71-6
  • Article Data51
  • CAS DataBase
  • Density 1.49 g/cm3
  • Solubility
  • Melting Point >260 °C (dec.)
  • Formula C15H11ClFN3O2
  • Boiling Point 478.809 °C at 760 mmHg
  • Molecular Weight 319.723
  • Flash Point 243.375 °C
  • Transport Information
  • Appearance tan solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 184475-71-6 (4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol)
  • Hazard Symbols
  • Synonyms 4-(3-Chloro-4-fluoroanilino)-6-hydroxy-7-methoxyquinazoline;4-(3-Chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline;N-(3-Chloro-4-fluorophenyl)-6-hydroxy-7-methoxyquinazolin-4-amine;
  • PSA 67.27000
  • LogP 3.95310

Synthetic route

4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate
788136-89-0

4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 20℃; for 13h; Inert atmosphere;99%
With sodium methylate In methanol for 3h; Reflux;95.3%
With methanol; ammonium hydroxide at 20℃; for 3h;95%
3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

2-amino-5-hydroxy-4-methoxybenzonitrile

2-amino-5-hydroxy-4-methoxybenzonitrile

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
With acetic acid In toluene at 65℃; for 7h; Solvent; Temperature; Concentration; Reagent/catalyst; Inert atmosphere;97%
...Expand
4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl acetate hydrochloride

4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl acetate hydrochloride

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Stage #1: 4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl acetate hydrochloride With lithium hydroxide; water In methanol at 20℃; for 0.5h;
Stage #2: With acetic acid In methanol; water		94%
With lithium hydroxide; water In methanol at 20℃; for 0.5h;94%
Stage #1: 4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl acetate hydrochloride With methanol; lithium hydroxide; water at 20℃; for 0.5h;
Stage #2: With acetic acid In water		94%
6-(benzyloxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine
913819-12-2

6-(benzyloxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
With methanesulfonic acid In chloroform for 5h; Reflux;91%
With trifluoroacetic acid at 75℃; for 4h;90%
With palladium 10% on activated carbon; hydrogen In methanol under 3102.97 Torr; for 24h;82%
N,N'-bis(3-chloro-4-fluorophenyl)formamidine
727658-04-0

N,N'-bis(3-chloro-4-fluorophenyl)formamidine

2-amino-5-hydroxy-4-methoxybenzonitrile

2-amino-5-hydroxy-4-methoxybenzonitrile

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 110℃; for 5h;84.2%
4-chloro-7-methoxyquinazolin-6-yl acetate hydrochloride salt

4-chloro-7-methoxyquinazolin-6-yl acetate hydrochloride salt

3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Stage #1: 4-chloro-7-methoxyquinazolin-6-yl acetate hydrochloride salt; 3-chloro-4-fluorophenylamine In N,N-dimethyl-formamide at 80℃; for 1h;
Stage #2: With ammonia; water In methanol for 2h; Reflux;		75%
C30H24ClFN3O4Pol

C30H24ClFN3O4Pol

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; not specified;44%
4-chloro-7-methoxyquinazolin-6-yl acetate hydrochloride salt

4-chloro-7-methoxyquinazolin-6-yl acetate hydrochloride salt

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: propan-2-ol / 5 h / 90 °C
2: 90 percent / ammonia / methanol; H2O / 24 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: toluene; isopropyl alcohol / 3 h / 20 - 65 °C
2: lithium hydroxide / water; methanol / 1 h / 20 °C
View Scheme
6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one
179688-53-0

6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / N,N-diethylaniline; phosphoryl chloride / 1 h / 80 - 100 °C
2: propan-2-ol / 5 h / 90 °C
3: 90 percent / ammonia / methanol; H2O / 24 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: SOCl2
2: NH4OH / methanol
View Scheme
Multi-step reaction with 3 steps
1: trichlorophosphate / toluene / Reflux
2: pyridine / isopropyl alcohol / Reflux
3: water; sodium hydroxide / methanol
View Scheme
3H-6,7-dimethoxyquinazolin-4-one
13794-72-4

3H-6,7-dimethoxyquinazolin-4-one

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: L-methionine; methanesulfonic acid / 12 h / Heating
2: pyridine; 4-(dimethylamino)pyridine / 6 h / 100 °C
3: 92 percent / N,N-diethylaniline; phosphoryl chloride / 1 h / 80 - 100 °C
4: propan-2-ol / 5 h / 90 °C
5: 90 percent / ammonia / methanol; H2O / 24 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: methionine; MeSO3H / 3 h / 100 °C
2: pyridine
3: SOCl2
4: NH4OH / methanol
View Scheme
Multi-step reaction with 5 steps
1: methanesulfonic acid; L-methionine / 120 °C
2: pyridine; dmap / 100 °C
3: trichlorophosphate / toluene / Reflux
4: pyridine / isopropyl alcohol / Reflux
5: water; sodium hydroxide / methanol
View Scheme
6-hydroxy-7-methoxyquinazolin-4(3H)-one
179688-52-9

6-hydroxy-7-methoxyquinazolin-4(3H)-one

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine; 4-(dimethylamino)pyridine / 6 h / 100 °C
2: 92 percent / N,N-diethylaniline; phosphoryl chloride / 1 h / 80 - 100 °C
3: propan-2-ol / 5 h / 90 °C
4: 90 percent / ammonia / methanol; H2O / 24 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: pyridine
2: SOCl2
3: NH4OH / methanol
View Scheme
Multi-step reaction with 4 steps
1: pyridine; dmap / 100 °C
2: trichlorophosphate / toluene / Reflux
3: pyridine / isopropyl alcohol / Reflux
4: water; sodium hydroxide / methanol
View Scheme
6-acetoxy-4-chloro-7-methoxyquinazoline
230955-75-6

6-acetoxy-4-chloro-7-methoxyquinazoline

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH4OH / methanol
View Scheme
Multi-step reaction with 2 steps
1: pyridine / isopropyl alcohol / Reflux
2: water; sodium hydroxide / methanol
View Scheme
Multi-step reaction with 2 steps
1: isopropyl alcohol / 5 h / 88 °C
2: water; sodium hydroxide / methanol / 6 h / 20 °C
View Scheme
2-carboethoxy-4,5-dimethoxyaniline
20323-74-4

2-carboethoxy-4,5-dimethoxyaniline

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 160 - 170 °C
2: methanesulfonic acid; L-methionine / 120 °C
3: pyridine; dmap / 100 °C
4: trichlorophosphate / toluene / Reflux
5: pyridine / isopropyl alcohol / Reflux
6: water; sodium hydroxide / methanol
View Scheme
Multi-step reaction with 6 steps
1: 165 - 170 °C
2: L-methionine; methanesulfonic acid
3: pyridine / 100 °C
4: thionyl chloride; N,N-dimethyl-formamide / 90 °C
5: isopropyl alcohol / Reflux
6: ammonia / water; methanol / 24 h / 20 °C
View Scheme
ethyl 2-nitro-4,5-dimethoxybenzoate
100905-33-7

ethyl 2-nitro-4,5-dimethoxybenzoate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: palladium on activated charcoal; hydrogen
2: 160 - 170 °C
3: methanesulfonic acid; L-methionine / 120 °C
4: pyridine; dmap / 100 °C
5: trichlorophosphate / toluene / Reflux
6: pyridine / isopropyl alcohol / Reflux
7: water; sodium hydroxide / methanol
View Scheme
Multi-step reaction with 7 steps
1: iron; hydrogenchloride / ethanol; water / Reflux
2: 165 - 170 °C
3: L-methionine; methanesulfonic acid
4: pyridine / 100 °C
5: thionyl chloride; N,N-dimethyl-formamide / 90 °C
6: isopropyl alcohol / Reflux
7: ammonia / water; methanol / 24 h / 20 °C
View Scheme
ethyl veratrate
3943-77-9

ethyl veratrate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: nitric acid; acetic acid / 0 - 5 °C
2: palladium on activated charcoal; hydrogen
3: 160 - 170 °C
4: methanesulfonic acid; L-methionine / 120 °C
5: pyridine; dmap / 100 °C
6: trichlorophosphate / toluene / Reflux
7: pyridine / isopropyl alcohol / Reflux
8: water; sodium hydroxide / methanol
View Scheme
Multi-step reaction with 8 steps
1: nitric acid / 0 °C
2: iron; hydrogenchloride / ethanol; water / Reflux
3: 165 - 170 °C
4: L-methionine; methanesulfonic acid
5: pyridine / 100 °C
6: thionyl chloride; N,N-dimethyl-formamide / 90 °C
7: isopropyl alcohol / Reflux
8: ammonia / water; methanol / 24 h / 20 °C
View Scheme
Veratric acid
93-07-2

Veratric acid

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: sulfuric acid / Reflux
2: nitric acid; acetic acid / 0 - 5 °C
3: palladium on activated charcoal; hydrogen
4: 160 - 170 °C
5: methanesulfonic acid; L-methionine / 120 °C
6: pyridine; dmap / 100 °C
7: trichlorophosphate / toluene / Reflux
8: pyridine / isopropyl alcohol / Reflux
9: water; sodium hydroxide / methanol
View Scheme
Multi-step reaction with 9 steps
1: sulfuric acid
2: nitric acid / 0 °C
3: iron; hydrogenchloride / ethanol; water / Reflux
4: 165 - 170 °C
5: L-methionine; methanesulfonic acid
6: pyridine / 100 °C
7: thionyl chloride; N,N-dimethyl-formamide / 90 °C
8: isopropyl alcohol / Reflux
9: ammonia / water; methanol / 24 h / 20 °C
View Scheme
2-Amino-4,5-dimethoxybenzoic acid
5653-40-7

2-Amino-4,5-dimethoxybenzoic acid

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: trimethyl orthoformate / methanol / 4 h / 70 °C / Reflux
2.1: methanesulfonic acid; DL-methionine / 3 h / 130 °C / Cooling with ice
2.2: pH 7
3.1: pyridine / 3 h / 20 - 100 °C
4.1: thionyl chloride / N,N-dimethyl-formamide / 3 h / 70 °C
5.1: isopropyl alcohol / 5 h / 88 °C
6.1: water; sodium hydroxide / methanol / 6 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: trimethyl orthoformate / methanol / 4 h / 70 °C
2: DL-methionine; methanesulfonic acid / 3 h / 130 °C
3: pyridine / 3 h / 100 °C
4: thionyl chloride / N,N-dimethyl-formamide / 3 h / 70 °C
5: isopropyl alcohol / 5 h / 88 °C
6: sodium hydroxide; methanol / 6 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: water / Microwave irradiation
2: magnesium sulfate; methanesulfonic acid
3: pyridine / 20 °C
4: triethylamine; trichlorophosphate / acetonitrile / 80 °C
5: 1,4-dioxane
6: sodium hydroxide / water; tetrahydrofuran / 4 h / 20 °C
View Scheme
methyl 2-amino-4,5-dimethoxybenzoate
26759-46-6

methyl 2-amino-4,5-dimethoxybenzoate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: formamide / 2 h / 190 - 200 °C
2: methanesulfonic acid; L-methionine / 5 h / 150 - 160 °C
3: pyridine / 3 h / Heating / reflux
4: trichlorophosphate / 3 h / Heating / reflux
5: isopropyl alcohol / 3 h / Heating / reflux
6: methanol; lithium hydroxide; water / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: methanol; N,N-dimethyl-formamide / Inert atmosphere
2: methanesulfonic acid; DL-methionine / Inert atmosphere
3: pyridine / Inert atmosphere
4: thionyl chloride / N,N-dimethyl-formamide / Inert atmosphere
5: isopropyl alcohol / Inert atmosphere
6: ammonium hydroxide / 3 h / Inert atmosphere; Reflux
View Scheme
3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; trichlorophosphate / toluene / 20 - 60 °C
1.2: 2 h / 65 °C
2.1: lithium hydroxide; water / methanol / 0.5 h / 20 °C
View Scheme
6-(benzyloxy)-4-chloro-7-methoxyquinazoline
286371-65-1

6-(benzyloxy)-4-chloro-7-methoxyquinazoline

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 60 - 65 °C
2: methanesulfonic acid / chloroform / 5 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: isopropyl alcohol / Reflux
2: trifluoroacetic acid / 1 h / Reflux
View Scheme
isovanillin
621-59-0

isovanillin

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: aminosulfonic acid; sodium chlorite / water / 2 h / 5 - 8 °C
2.1: hydrogenchloride / 4 h / 50 - 55 °C
3.1: potassium carbonate; potassium iodide / acetone / 25 - 30 °C
3.2: Reflux
4.1: nitric acid; acetic acid / 14 h / 25 - 35 °C
5.1: acetic acid; iron / 50 - 60 °C
6.1: ethyl acetate / 12 h / Reflux
7.1: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / chloroform / 12 h / 60 - 65 °C
8.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 60 - 65 °C
9.1: methanesulfonic acid / chloroform / 5 h / Reflux
View Scheme
Multi-step reaction with 7 steps
1: sodium formate; formic acid; hydroxyammonium sulfate / 85 °C
2: potassium carbonate / acetonitrile / 1.5 h / Reflux
3: acetic acid; nitric acid / 1 h / Cooling with ice
4: tin(ll) chloride; hydrogenchloride / water; acetic acid / 1 h / 60 °C
5: acetic acid / benzene / 2 h / 105 °C / Dean-Stark
6: acetic acid / 3 h / 130 - 140 °C
7: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 3102.97 Torr
View Scheme
Isovanillic acid
645-08-9

Isovanillic acid

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: hydrogenchloride / 4 h / 50 - 55 °C
2.1: potassium carbonate; potassium iodide / acetone / 25 - 30 °C
2.2: Reflux
3.1: nitric acid; acetic acid / 14 h / 25 - 35 °C
4.1: acetic acid; iron / 50 - 60 °C
5.1: ethyl acetate / 12 h / Reflux
6.1: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / chloroform / 12 h / 60 - 65 °C
7.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 60 - 65 °C
8.1: methanesulfonic acid / chloroform / 5 h / Reflux
View Scheme
Multi-step reaction with 8 steps
1: sulfuric acid / methanol / Reflux
2: potassium carbonate / butanone / Reflux
3: nitric acid; acetic acid / 30 °C
4: iron; ammonium chloride / methanol; water / Reflux
5: acetic acid; formamide / Reflux
6: trichlorophosphate; N,N-dimethyl-formamide / Reflux
7: isopropyl alcohol / Reflux
8: trifluoroacetic acid / 1 h / Reflux
View Scheme
3-hydroxy-4-methoxybenzoate
6702-50-7

3-hydroxy-4-methoxybenzoate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: potassium carbonate; potassium iodide / acetone / 25 - 30 °C
1.2: Reflux
2.1: nitric acid; acetic acid / 14 h / 25 - 35 °C
3.1: acetic acid; iron / 50 - 60 °C
4.1: ethyl acetate / 12 h / Reflux
5.1: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / chloroform / 12 h / 60 - 65 °C
6.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 60 - 65 °C
7.1: methanesulfonic acid / chloroform / 5 h / Reflux
View Scheme
Multi-step reaction with 7 steps
1: potassium carbonate / butanone / Reflux
2: nitric acid; acetic acid / 30 °C
3: iron; ammonium chloride / methanol; water / Reflux
4: acetic acid; formamide / Reflux
5: trichlorophosphate; N,N-dimethyl-formamide / Reflux
6: isopropyl alcohol / Reflux
7: trifluoroacetic acid / 1 h / Reflux
View Scheme
methyl 3-(benzyloxy)-4-methoxy-benzoate
57535-57-6

methyl 3-(benzyloxy)-4-methoxy-benzoate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: nitric acid; acetic acid / 14 h / 25 - 35 °C
2: acetic acid; iron / 50 - 60 °C
3: ethyl acetate / 12 h / Reflux
4: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / chloroform / 12 h / 60 - 65 °C
5: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 60 - 65 °C
6: methanesulfonic acid / chloroform / 5 h / Reflux
View Scheme
Multi-step reaction with 6 steps
1: nitric acid; acetic acid / 30 °C
2: iron; ammonium chloride / methanol; water / Reflux
3: acetic acid; formamide / Reflux
4: trichlorophosphate; N,N-dimethyl-formamide / Reflux
5: isopropyl alcohol / Reflux
6: trifluoroacetic acid / 1 h / Reflux
View Scheme
methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate
164161-49-3

methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: acetic acid; iron / 50 - 60 °C
2: ethyl acetate / 12 h / Reflux
3: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / chloroform / 12 h / 60 - 65 °C
4: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 60 - 65 °C
5: methanesulfonic acid / chloroform / 5 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1: iron; ammonium chloride / methanol; water / Reflux
2: acetic acid; formamide / Reflux
3: trichlorophosphate; N,N-dimethyl-formamide / Reflux
4: isopropyl alcohol / Reflux
5: trifluoroacetic acid / 1 h / Reflux
View Scheme
methyl 2-amino-5-(benzyloxy)-4-methoxybenzoate
855793-63-4

methyl 2-amino-5-(benzyloxy)-4-methoxybenzoate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethyl acetate / 12 h / Reflux
2: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / chloroform / 12 h / 60 - 65 °C
3: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 60 - 65 °C
4: methanesulfonic acid / chloroform / 5 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: acetic acid; formamide / Reflux
2: trichlorophosphate; N,N-dimethyl-formamide / Reflux
3: isopropyl alcohol / Reflux
4: trifluoroacetic acid / 1 h / Reflux
View Scheme
6-(benzyloxy)-7-methoxyquinazolin-4(3H)-one
286371-64-0

6-(benzyloxy)-7-methoxyquinazolin-4(3H)-one

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / chloroform / 12 h / 60 - 65 °C
2: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 60 - 65 °C
3: methanesulfonic acid / chloroform / 5 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: trichlorophosphate; N,N-dimethyl-formamide / Reflux
2: isopropyl alcohol / Reflux
3: trifluoroacetic acid / 1 h / Reflux
View Scheme
C18H19N3O2

C18H19N3O2

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid / 3 h / 130 - 140 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 3102.97 Torr
View Scheme
2-methoxy-5-cyanophenol
52805-46-6

2-methoxy-5-cyanophenol

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: potassium carbonate / acetonitrile / 1.5 h / Reflux
2: acetic acid; nitric acid / 1 h / Cooling with ice
3: tin(ll) chloride; hydrogenchloride / water; acetic acid / 1 h / 60 °C
4: acetic acid / benzene / 2 h / 105 °C / Dean-Stark
5: acetic acid / 3 h / 130 - 140 °C
6: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 3102.97 Torr
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / methanol / 1 h / 65 °C / Inert atmosphere
2: nitric acid; acetic acid / 0 - 25 °C / Inert atmosphere
3: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 20 °C / 1520.1 - 2280.15 Torr
4: acetic acid / toluene / 7 h / 65 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate / methanol / 1 h / 65 °C / Inert atmosphere
2: nitric acid; acetic acid / 0 - 25 °C / Inert atmosphere
3: tetrabutylammomium bromide; sodium dithionite; water / methanol / 30 °C / Inert atmosphere
4: acetic acid / 110 °C / Inert atmosphere
5: trifluoroacetic acid / 4 h / 75 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetonitrile / 0.17 h / 20 °C
1.2: 5 h / Reflux
2.1: acetic acid; nitric acid / 1 h / Cooling with ice
3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2327.23 Torr
4.1: toluene-4-sulfonic acid / toluene / 5 h / 110 °C
View Scheme
propargyl bromide
106-96-7

propargyl bromide

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

4-(3'-chloro-4'-fluoroanilino)-6-(prop-2-ynyloxy)-7-methoxyquinazoline
1214731-77-7

4-(3'-chloro-4'-fluoroanilino)-6-(prop-2-ynyloxy)-7-methoxyquinazoline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;99%
tert-butyl 3-[2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]propanoate
217817-01-1

tert-butyl 3-[2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]propanoate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

3-(2-(2-(2-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)ethoxy)ethoxy)ethoxy)tert-butyl propionate

3-(2-(2-(2-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)ethoxy)ethoxy)ethoxy)tert-butyl propionate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;98.5%
(E)-methyl 3-(4-(2-(tosyloxy)ethoxy)phenyl)acrylate
1012057-56-5

(E)-methyl 3-(4-(2-(tosyloxy)ethoxy)phenyl)acrylate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

(E)-methyl 3-(4-(2-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)ethoxy)phenyl) acrylate
1012057-57-6

(E)-methyl 3-(4-(2-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)ethoxy)phenyl) acrylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;98%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;98%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;98%
trifluoroacetic acid
76-05-1

trifluoroacetic acid

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

tert-butyl 4-(3-bromopropyl)-piperazine-1-carboxylate
655225-02-8

tert-butyl 4-(3-bromopropyl)-piperazine-1-carboxylate

C27H33ClFN5O4*C2HF3O2

C27H33ClFN5O4*C2HF3O2

Conditions
ConditionsYield
Stage #1: 4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline; tert-butyl 4-(3-bromopropyl)-piperazine-1-carboxylate With potassium carbonate In N,N-dimethyl-formamide at 80℃;
Stage #2: trifluoroacetic acid In methanol; water		97%
...Expand
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

4-(3'-chloro-4'-fluorophenylamino)-7-methoxy-6-(trifluoromethanesulfonyloxy)quinazoline
451494-86-3

4-(3'-chloro-4'-fluorophenylamino)-7-methoxy-6-(trifluoromethanesulfonyloxy)quinazoline

Conditions
ConditionsYield
With pyridine at 0 - 20℃; Inert atmosphere;94%
With pyridine at -6 - 20℃;62%
N-phthaloylglycine chloride
6780-38-7

N-phthaloylglycine chloride

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

C25H16ClFN4O5

C25H16ClFN4O5

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 4.5h; Inert atmosphere; Cooling with ice;93.2%
1-bromo-6-hexanol
4286-55-9

1-bromo-6-hexanol

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

6-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)hexan-1-ol
1012057-92-9

6-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)hexan-1-ol

Conditions
ConditionsYield
Stage #1: 4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 0.166667h;
Stage #2: 1-bromo-6-hexanol In N,N-dimethyl-formamide at 60℃; for 6h;		93%
methanesulfonic acid 2-[2-(2-{2-[3-(2,2,2-trifluoro-1,1-bis-trifluoromethyl-ethoxy)-2,2-bis-(2,2,2-trifluoro-1,1-bis-trifluoromethyl-ethoxymethyl)-propoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl ester
939056-49-2

methanesulfonic acid 2-[2-(2-{2-[3-(2,2,2-trifluoro-1,1-bis-trifluoromethyl-ethoxy)-2,2-bis-(2,2,2-trifluoro-1,1-bis-trifluoromethyl-ethoxymethyl)-propoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl ester

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-((18,18,18-trifluoro-14,14-bis(((1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl)oxy)methyl)-17,17-bis(trifluoromethyl)-3,6,9,12,16-pentaoxaoctadecyl)oxy)quinazolin-4-amine

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-((18,18,18-trifluoro-14,14-bis(((1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl)oxy)methyl)-17,17-bis(trifluoromethyl)-3,6,9,12,16-pentaoxaoctadecyl)oxy)quinazolin-4-amine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;93%
10-(3-chloropropyl)-1,4,7,10-tetraazacyclododecan-1,4,7-tricarboxylic acid tri-tert-butyl ester

10-(3-chloropropyl)-1,4,7,10-tetraazacyclododecan-1,4,7-tricarboxylic acid tri-tert-butyl ester

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

10-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)-1,4,7,10-tetraazacyclododecan-1,4,7-tricarboxylic acid tri-tert-butyl ester

10-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)-1,4,7,10-tetraazacyclododecan-1,4,7-tricarboxylic acid tri-tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 6h;92.8%
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 6h;66%
4-(3-chloropropyl)morpholine
7357-67-7

4-(3-chloropropyl)morpholine

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 3h; Reagent/catalyst; Temperature;92%
With tetrabutylammomium bromide; sodium carbonate; potassium iodide In iso-butanol Reflux;90%
In N,N-dimethyl-formamide at 80 - 90℃; Concentration;88%
1-chloro-3-hydroxypropane
627-30-5

1-chloro-3-hydroxypropane

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

M 527301
1221965-74-7

M 527301

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile for 12h; Reflux;91%
7-(3-chloropropyl)-1,4,7-triazacyclononan-1,4-dicarboxylic acid di-tert-butyl ester

7-(3-chloropropyl)-1,4,7-triazacyclononan-1,4-dicarboxylic acid di-tert-butyl ester

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

7-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)-1,4,7-triazacyclononan-1,4-dicarboxylic acid di-tert-butyl ester

7-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)-1,4,7-triazacyclononan-1,4-dicarboxylic acid di-tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 6h;89.8%
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 6h;66%
3-morpholinopropyl 4-methylbenzenesulfonate
957621-67-9

3-morpholinopropyl 4-methylbenzenesulfonate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Solvent; Temperature;89.5%
methanesulfonic acid 3-morpholin-4-yl-propyl ester
1018895-28-7

methanesulfonic acid 3-morpholin-4-yl-propyl ester

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Solvent; Temperature;89.2%
1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

6-(3-chloropropoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-ylamine
912556-91-3

6-(3-chloropropoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-ylamine

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 40℃; for 6h;89%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 40℃; for 6h;89%
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 4h;
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 4h; Heating;Ca. 330 mg
ethyl 5-bromovalerate
14660-52-7

ethyl 5-bromovalerate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

ethyl 4-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)pentanoate

ethyl 4-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)pentanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 0.5h;88%
4-(3-chloropropyl)morpholine
7357-67-7

4-(3-chloropropyl)morpholine

ethylene glycol
107-21-1

ethylene glycol

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

gefitinib ethylene glycol

gefitinib ethylene glycol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃; for 8h;85.9%
...Expand
allyl bromide
106-95-6

allyl bromide

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

(6-allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine

(6-allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine

Conditions
ConditionsYield
With potassium carbonate In acetone at 90℃; for 4h;82%
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

ethyl 4-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)butanoate
1012057-14-5

ethyl 4-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)butanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 0.5h;81%
ethyl 17-[[(4-methylbenzene)sulfonyl]oxy]-3,6,9,12,15-pentaoxaheptadecanoate

ethyl 17-[[(4-methylbenzene)sulfonyl]oxy]-3,6,9,12,15-pentaoxaheptadecanoate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

ethyl 1-[4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl]-1,4,7,10,13,16-hexaoxaoctadecan-18-oate

ethyl 1-[4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl]-1,4,7,10,13,16-hexaoxaoctadecan-18-oate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;80%
4-benzyl-6-(3-chloropropyl)octahydropyrrolo[3,4-b][1,4]oxazine

4-benzyl-6-(3-chloropropyl)octahydropyrrolo[3,4-b][1,4]oxazine

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

6-(3-(4-benzylhexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl)propoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine
1438075-59-2

6-(3-(4-benzylhexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl)propoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 18h;79.59%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 18h;79.59%
2-bromoethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
86651-36-7

2-bromoethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

2-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)ethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside

2-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)ethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside

Conditions
ConditionsYield
Stage #1: 4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #2: 2-bromoethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside In N,N-dimethyl-formamide at 80℃; for 8h; Inert atmosphere;		79%
4 (3-bromopropyl)-morpholine
125422-83-5

4 (3-bromopropyl)-morpholine

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 12h;78%
2-(3-chloropropyl)octahydrocyclopenta[c]pyrrole
1438081-50-5

2-(3-chloropropyl)octahydrocyclopenta[c]pyrrole

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

N-(3-chloro-4-fluorophenyl)-6-(3-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)propoxy)-7-methoxyquinazolin-4-amine
1438073-01-8

N-(3-chloro-4-fluorophenyl)-6-(3-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)propoxy)-7-methoxyquinazolin-4-amine

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;75.59%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere;

4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol Chemical Properties

Following is the structure of 4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol (CAS NO.184475-71-6):
                       
Empirical Formula: C15H11ClFN3O2
Molecular Weight: 319.7181 
Index of Refraction: 1.702
Molar Refractivity: 83.101 cm3
Molar Volume: 214.63 cm3
Density: 1.49 g/cm3
Flash Point: 243.375 °C 
Melting point: >260 °C (dec.)
Polarizability: 32.944 10-24cm3
Surface Tension: 64.15 dyne/cm
Enthalpy of Vaporization: 77.132 kJ/mol
Boiling Point: 478.809 °C at 760 mmHg 
Appearance of 4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol (CAS NO.184475-71-6): Tan Solid
Product Categories: Various Metabolites and Impurities; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals
SMILES: Fc1ccc(cc1Cl)Nc3ncnc2c3cc(O)c(OC)c2
InChI: InChI=1/C15H11ClFN3O2/c1-22-14-6-12-9(5-13(14)21)15(19-7-18-12)20-8-2-3-11(17)10(16)4-8/h2-7,21H,1H3,(H,18,19,20)
InChIKey: JLVTVCRXFMLUIF-UHFFFAOYAN

4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol Uses

 4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol (CAS NO.184475-71-6) can be uesd as a metabolite of Gefitinib.

4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol Specification

 4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol , its cas register number 184475-71-6. It also can be called N-(3-Chloro-4-fluorophenyl)-6-hydroxy-7-methoxyquinazolin-4-amine ; and 6-Quinazolinol, 4-[(3-chloro-4-fluorophenyl)amino]-7-methoxy- .

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