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

HRID 566947Notes

Reaction equation

HRID 566947 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 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-437be30a41fc4a1ca73ea8c436dbf42f
Source dataset
uspto-grants-2001_01
Patent number
US06177433B1

Reaction notes

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