Ammonia → 3,4-Dimethoxy-6-nitrobenzamide

HRID 392177

Reaktionsgleichung

Reaktionsgleichung von HRID 392177
[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-b1a56db9ed184ae2822cd44cd51538db
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800649B1

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