Ammonia → 3,4-Dimethoxy-6-nitrobenzamide

HRID 427423

反応式

HRID 427423 の反応式
[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

参加物

4

実験手順

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).

出典と根拠

ORDレコード
ord-8be6a258a91d45d784672c58bba29202
出典データセット
uspto-grants-2001_11
特許番号
US06313130B1

関連ノート

読み込み中…