7-Chloroquinazolin-4(3H)-one supplier

Name
7-CHLORO-4-QUINAZOLINOL
EINECS 207-219-2
CAS No. 31374-18-2
Article Data79
CAS DataBase
Density 1.5 g/cm³
Solubility
Melting Point 251-253 °C
Formula C₈H₅ClN₂O
Boiling Point 331.7 °C at 760 mmHg
Molecular Weight 180.593
Flash Point 154.4 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 7-Chloro-4(3H)-quinazolinone;7-Chloro-4(3H)-quinazolone;7-Chloro-4-quinazolinol;7-Chloroquinazolin-4-one;NSC 44057;4(1H)-Quinazolinone,7-chloro- (6CI,9CI);7-Chloro-3,4-dihydroquinazolin-4-one;7-Chloro-3H-quinazolin-4-one;
PSA 46.01000
LogP 1.98880

Synthetic route

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 89-77-0
2-Amino-4-chlorobenzoic acid

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With acetic acid; diethylamine at 150℃; for 2h; Product distribution / selectivity;	96.1%
With montmorillonite K-10 for 0.0666667h; microwave irradiation;	94%
at 130 - 160℃; for 5h;	90.7%

: 3473-63-0
formamidine acetic acid

: 89-77-0
2-Amino-4-chlorobenzoic acid

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
In water Microwave irradiation;	95%
In 2-methoxy-ethanol at 120℃; for 16h;	88.1%
In 2-methoxy-ethanol Reflux;
In 2-methoxy-ethanol for 18h; Reflux;
In 2-methoxy-ethanol at 130℃;

: 67-56-1
methanol

: 38487-86-4
2-amino-4-chlorobenzonitrile

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With cobalt(II) nitrate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine; water; caesium carbonate at 150℃; for 36h; Inert atmosphere; Sealed tube;	92%

: 64392-62-7
formamidinium acetate

: 89-77-0
2-Amino-4-chlorobenzoic acid

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
In 2-methoxy-ethanol for 1.5h; Heating;	89%

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
at 130 - 190℃; for 4.5h;	87.7%

: 153437-17-3
6-amino-7-methoxy-4-(3'-methylanilino)quinazoline

: 111-90-0
ethoxyethoxyethanol

: 89-77-0
2-Amino-4-chlorobenzoic acid

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With formamide	85%

...Expand

: 67-56-1
methanol

: 5900-59-4
2-amino-4-chlorobenzamide

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With copper(l) iodide; oxygen; caesium carbonate at 20℃; for 16h; Irradiation;	85%
With [Cp*Ir(2,2′-bpyO)(H2O)]; caesium carbonate at 130℃; for 2h; Microwave irradiation; Green chemistry;	70%
With [Cp*Ir(2,2'-bpyO)(H2O)]; caesium carbonate at 130℃; for 2h; Inert atmosphere; Microwave irradiation;	70%
With oxygen; copper(II) acetate monohydrate; caesium carbonate at 110℃; for 6h;	68%

: 5900-58-3
2-amino-4-chloro-benzoic acid methyl ester

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With acetic acid; diethylamine at 150℃; for 2h; Product distribution / selectivity;	84.1%
With formic acid at 145℃; for 12h;	81%
Niementowski Quinazolone Synthesis;
for 10h; Reflux;

: 5900-59-4
2-amino-4-chlorobenzamide

: 144-62-7
oxalic acid

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
In 1,4-dioxane at 120℃; for 14h; Green chemistry;	83%

: 6313-33-3
formamidine hydrochloride

: 89-77-0
2-Amino-4-chlorobenzoic acid

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
at 210℃; for 0.25h; Cycloaddition;	81%

: 5900-59-4
2-amino-4-chlorobenzamide

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With hydrogenchloride In water; trimethyl orthoformate	77%

: 942319-20-2
4-chloro-2-iodobenzamide

: 463-52-5
formamidine

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;	71%

: 2516-95-2
5-chloro-2-nitrobenzoic acid

: 16712-16-6, 64165-14-6, 65387-22-6, 70179-79-2, 540-69-2
ammonium formate

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With zinc for 0.108333h; microwave irradiation;	70%

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: C24H24Cl2N2O6

A: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

B: C24H22Cl2N4O2

Conditions

Conditions	Yield
at 186℃;	A 16.2% B 51.5%

...Expand

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: C23H22Cl2N2O6

A: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: C23H20Cl2N4O2

Conditions

Conditions	Yield
at 180 - 185℃; for 2h;	A 19.9% B 47.5%

...Expand

: 38487-86-4
2-amino-4-chlorobenzonitrile

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

A: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

B: 13165-35-0
7-chloroquinazoline-2,4-dione

Conditions

Conditions	Yield
With zinc(II) chloride at 200℃; for 5h; sealed tube;	A 35% B 36%

...Expand

: 5900-59-4
2-amino-4-chlorobenzamide

: 122-51-0
orthoformic acid triethyl ester

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With diethylene glycol at 120℃;

: 5900-59-4
2-amino-4-chlorobenzamide

: 149-73-5
trimethyl orthoformate

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
With hydrogenchloride

: 89-77-0
2-Amino-4-chlorobenzoic acid

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / Et3N / dioxane / 2 h / 20 °C 2: 16.2 percent / 186 °C View Scheme
Multi-step reaction with 2 steps 1: 74.4 percent / Et3N / dioxane / 3 h / 20 °C 2: 19.9 percent / 2 h / 180 - 185 °C View Scheme
With formamide for 5h; Heating / reflux;
Multi-step reaction with 2 steps 1: sulfuric acid / 9 h / Cooling with ice; Reflux 2: formic acid / 12 h / 145 °C View Scheme
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; ammonium chloride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 15 h / 20 °C 2: copper(l) iodide; caesium carbonate; oxygen / 16 h / 20 °C / Irradiation View Scheme

: 123-91-1
1,4-dioxane

: 5900-59-4
2-amino-4-chlorobenzamide

: 122-51-0
orthoformic acid triethyl ester

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one

...Expand

: 6280-88-2
4-chloro-2-nitro-benzoic acid

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium formate; 5%-palladium/activated carbon / ethanol / 6 h / Reflux 2: 4 h / Reflux View Scheme

: 74-11-3
para-chlorobenzoic acid

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid / water / 6 h / 60 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / ethanol / 6 h / Reflux 3: 4 h / Reflux View Scheme

: 122-51-0
orthoformic acid triethyl ester

: 89-77-0
2-Amino-4-chlorobenzoic acid

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
at 100℃; for 17h;
With ammonium acetate In ethanol at 110℃; for 0.333333h; Microwave irradiation;

: 89-77-0
2-Amino-4-chlorobenzoic acid

: 463-52-5
formamidine

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
In 2-methoxy-ethanol at 130℃;

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 2969-81-5
4-bromoethylbutanoate

: 4-(7-chloro-4-oxo-4H-quinazolin-3-yl)-butyric acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 10h; Alkylation;	97%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 160879-62-9
methyl 1-phenylprop-2-enyl carbonate

: 7-chloro-3-((S)-1-phenylallyl)quinazolin-4(3H)-one

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;	96%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 100-46-9
benzylamine

: 477861-82-8
N-benzyl-7-chloroquinazolin-4-amine

Conditions

Conditions	Yield
With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane at 125℃; for 2h;	95%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 2148-57-4
4,7-dichloroquinazoline

Conditions

Conditions	Yield
With trichlorophosphate at 100℃; for 3h;	94.828%
With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 20 - 60℃;	80%
With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 60℃; Cooling with ice;	80%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 1539-59-9
4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

: 7-chloro-2-cyclohexylquinazolin-4(3H)-one

Conditions

Conditions	Yield
Stage #1: 7-chloro-3,4-dihydroquinazolin-4-one; 4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester With trifluoroacetic acid In 2,2,2-trifluoroethanol at 20℃; for 4h; Sealed tube; Irradiation; Inert atmosphere; Stage #2: In 2,2,2-trifluoroethanol at 20℃; for 4h;	93%
Stage #1: 7-chloro-3,4-dihydroquinazolin-4-one; 4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 4h; Irradiation; Inert atmosphere; Sealed tube; Stage #2: In 2,2,2-trifluoroethanol for 4h; Irradiation; Inert atmosphere;	93%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 53449-14-2
7-chloro-6-nitro-4(3H)-quinazolinone

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 50 - 90℃;	92.6%
With sulfuric acid; nitric acid at 0 - 90℃; for 3h;	72%
With sulfuric acid; nitric acid at 90℃; for 3h; Cooling with ice;	71.2%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 147804-30-6
1-oxa-6-aza-spiro-[2.5]octane-6-caboxylic acid tert-butyl ester

: 1426340-66-0
tert-butyl 4-[(7-chloro-4-oxo-3,4-dihydroquinazolin-3-yl)methyl]-4-hydroxypiperidine-1-carboxylate

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃;	85%
With caesium carbonate In N,N-dimethyl-formamide at 80℃;	85%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;	83.7%
With caesium carbonate In N,N-dimethyl-formamide at 80℃;	68%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 100-11-8
1-bromomethyl-4-nitro-benzene

: 7-chloro-3-(4-nitro-benzyl)-3H-quinazolin-4-one

Conditions

Conditions	Yield
Stage #1: 7-chloro-3,4-dihydroquinazolin-4-one With sodium methylate In methanol for 0.166667h; Metallation; Stage #2: 1-bromomethyl-4-nitro-benzene In methanol at 20℃; for 0.5h; Condensation;	81.6%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 2114-00-3
2-bromo-1-phenyl-1-propanone

: 7-chloro-3-(1-methyl-2-oxo-2-phenyl-ethyl)-3H-quinazolin-4-one

Conditions

Conditions	Yield
Stage #1: 7-chloro-3,4-dihydroquinazolin-4-one With sodium methylate In methanol for 0.166667h; Metallation; Stage #2: 2-bromo-1-phenyl-1-propanone In methanol at 20℃; for 0.5h; Condensation;	79.4%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 403-29-2
2-bromo-4'-fluoroacetophenone

: 7-chloro-3-[2-(4-fluoro-phenyl)-2-oxo-ethyl]-3H-quinazolin-4-one

Conditions

Conditions	Yield
Stage #1: 7-chloro-3,4-dihydroquinazolin-4-one With sodium methylate In methanol for 0.166667h; Metallation; Stage #2: 2-bromo-4'-fluoroacetophenone In methanol at 20℃; for 0.5h; Condensation;	77.8%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 402-49-3
4-bromomethyltrifluoromethylbenzene

: 7-chloro-3-(4-trifluoromethyl-benzyl)-3H-quinazolin-4-one

Conditions

Conditions	Yield
Stage #1: 7-chloro-3,4-dihydroquinazolin-4-one With sodium methylate In methanol for 0.166667h; Metallation; Stage #2: 4-bromomethyltrifluoromethylbenzene In methanol at 20℃; for 0.5h; Condensation;	76.9%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 110-82-7
cyclohexane

: 7-chloro-2-cyclohexylquinazolin-4(3H)-one

Conditions

Conditions	Yield
With sodium azide; bis-[(trifluoroacetoxy)iodo]benzene In 2,2,2-trifluoroethanol at 20℃; for 3h;	76%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 70-11-1
α-bromoacetophenone

: 7-chloro-3-(2-oxo-2-phenyl-ethyl)-3H-quinazolin-4-one

Conditions

Conditions	Yield
Stage #1: 7-chloro-3,4-dihydroquinazolin-4-one With sodium methylate In methanol for 0.166667h; Metallation; Stage #2: α-bromoacetophenone In methanol at 20℃; for 0.5h; Condensation;	75%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 459-46-1
4-Fluorobenzyl bromide

: 7-chloro-3-(4-fluorophenylmethyl)quinazolin-4(3H)-one

Conditions

Conditions	Yield
Stage #1: 7-chloro-3,4-dihydroquinazolin-4-one With sodium methylate In methanol for 0.166667h; Metallation; Stage #2: 4-Fluorobenzyl bromide In methanol at 20℃; for 0.5h; Condensation;	74.5%

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 78-95-5
chloroacetone

: 7-chloro-3-(2-oxopropyl)quinazolin-4(3H)-one

Conditions

Conditions	Yield
Stage #1: 7-chloro-3,4-dihydroquinazolin-4-one With sodium hydride In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h; Stage #2: chloroacetone In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h;	74%

: 100-43-6
4-vinylpyridine

: 31374-18-2
7-chloro-3,4-dihydroquinazolin-4-one

: 7-chloro-3-(2-(pyridin-4-yl)ethyl)quinazolin-4(3H)-one

Conditions

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In toluene at 110℃; Inert atmosphere;	73%

7-Chloroquinazolin-4(3H)-one Specification

The 7-Chloroquinazolin-4(3H)-one, its cas register number is 31374-18-2. It also can be called as 4(3H)-Quinazolinone,7-chloro- and the IUPAC name about this chemical is 7-chloro-1H-quinazolin-4-one. It belongs to the following product categories, such as Alcohols and Derivatives and Heterocycles.

Physical properties about 7-Chloroquinazolin-4(3H)-one are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 3; (6)#H bond donors: 1; (7)Polar Surface Area: 46.01Å²; (8)Index of Refraction: 1.71; (9)Molar Refractivity: 47.055 cm³; (10)Molar Volume: 120.377 cm³; (11)Polarizability: 18.654x10^-24cm³; (12)Surface Tension: 71.697 dyne/cm; (13)Enthalpy of Vaporization: 62.939 kJ/mol

Preparation: this chemical can be prepared by formamide and 2-amino-4-chloro-benzoic acid. This reaction will need reagent montmorillonite K-10 and microwave irradiation. The reaction time is 4 min. The yield is about 94 %.

Uses of 7-chloro-3H-quinazolin-4-one : it can be used to react with 4-bromo-butyric acid ethyl ester to produce 4-(7-chloro-4-oxo-4H-quinazolin-3-yl)-butyric acid ethyl ester. This reaction is a kind of Alkylation. It will need reagent dimethylformamide and K₂CO₃. The reaction time is 10 hour(s) with reaction temperature of 70 ℃. The yield is about 97 %.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC2=C(C=C1Cl)NC=NC2=O
(2)InChI: InChI=1S/C8H5ClN2O/c9-5-1-2-6-7(3-5)10-4-11-8(6)12/h1-4H,(H,10,11,12)
(3)InChIKey: PMLONMIODRHERC-UHFFFAOYSA-N

Product Name

7-CHLORO-4-QUINAZOLINOL

Synthetic route

7-Chloroquinazolin-4(3H)-one Specification

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