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

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

 EINECS 1806241-263-5
CAS No. 184475-71-6 Density 1.49 g/cm3
PSA 67.27000 LogP 3.95310
Solubility N/A 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 N/A Appearance tan solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 184475-71-6 (4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol) Hazard Symbols N/A
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;

Article Data 51

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

788136-89-0

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

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%
367-21-5

3-chloro-4-fluorophenylamine

2-amino-5-hydroxy-4-methoxybenzonitrile

4637-24-5

N,N-dimethyl-formamide dimethyl acetal

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%

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

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%
913819-12-2

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

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%
727658-04-0

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

2-amino-5-hydroxy-4-methoxybenzonitrile

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

367-21-5

3-chloro-4-fluorophenylamine

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

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

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
179688-53-0

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

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
13794-72-4

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

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

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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