3,4-Dimethoxy-6-nitrobenzamide → 2-Amino-4,5-dimethoxybenzamide

HRID 1421862Notes

Reaction equation

HRID 1421862 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:14]([O-])=O)[CH:4]=1.[BH4-].[Na+]>S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH2:14])[CH:4]=1

Participants

4

Reactant 2

HCID 27361933,4-Dimethoxy-6-nitrobenzamideHCID 4311764Sodium borohydride

Product 1

HCID 108672362-Amino-4,5-dimethoxybenzamide

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

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 cyclizcd 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-318e5f5e54104c79b136414142c53ddd
Source dataset
uspto-grants-2000_06
Patent number
US06080747

Reaction notes

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