Ammonia → 3,4-Dimethoxy-6-nitrobenzamide

HRID 427423

Reaktionsgleichung

Reaktionsgleichung von HRID 427423
[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

Komponenten

4

Edukt 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 786904,5-Dimethoxy-2-nitrobenzoic acid

Produkt 1

HCID 27361933,4-Dimethoxy-6-nitrobenzamide

Versuchsvorschrift

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).

Quellen und Nachweise

ORD-Eintrag
ord-8be6a258a91d45d784672c58bba29202
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313130B1

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