Ammonia → 3,4-Dimethoxy-6-nitrobenzamide

HRID 392177

Reaction equation

[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1.S(Cl)(Cl)=O.[NH3:21]>>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]([C:7]([NH2:21])=[O:8])=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 24386Thionyl Chloride

HCID 786904,5-Dimethoxy-2-nitrobenzoic acid

Product 1

HCID 27361933,4-Dimethoxy-6-nitrobenzamide

Procedure

4,5-Dimethoxy-2-nitrobenzoic acid (3) was treated with thionyl chloride and then reacted with ammonia to give 4,5-dimethoxy-2-nitrobenzamide (4) as described by F. Nomoto et al. Chem. Pharm. Bull. 1990, 38, 1591-1595. The nitro group in compound (4) was reduced with sodium borohydride in the presence of copper sulfate (see C. L. Thomas Catalytic Processes and Proven Catalysts Academic Press, New York (1970)) to give 4,5-dimethoxy-2-aminobenzamide (5) which was cyclized by refluxing with formic acid to give 6,7-dimethoxyquinazoline-4(3H)-one (6). Compound (6) was refluxed with phosphorus oxytrichloride to provide the common synthetic precursor (7).

Sources & evidence

ORD record: ord-b1a56db9ed184ae2822cd44cd51538db
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800649B1

Linked notes

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