The title compd. (I), an intermediate for antibacterial aditoprim, useful in veterinary medicine, is prepd. via bromination or chlorination of 4-(dimethylamino)benzonitrile (II), treatment of the resulting 3,5-dibromo- (III) or -dichloro-4-(methylamino)benzonitrile with alkali methoxide in the presence of Cu and DMF or dimethylacetamide, methylation of the resulting 3,5-dimethoxy-4-(methylamino)benzonitrile (IV), and redn. of the resulting 3,5-dimethoxy-4-(dimethylamino)benzonitrile. II in MeOH was brominated with aq. HBr, the resulting III treated with MeONa/MeOH and CuCl, and the resulting IV methylated with HCO2H/paraformaldehyde followed by redn. with Raney Ni to give I.
Preparation of 4-(dimethylamino)-3,5-dimethoxybenzaldehyde as intermediate for antibacterials
ZAGOTTO, GIUSEPPE
1989
Abstract
The title compd. (I), an intermediate for antibacterial aditoprim, useful in veterinary medicine, is prepd. via bromination or chlorination of 4-(dimethylamino)benzonitrile (II), treatment of the resulting 3,5-dibromo- (III) or -dichloro-4-(methylamino)benzonitrile with alkali methoxide in the presence of Cu and DMF or dimethylacetamide, methylation of the resulting 3,5-dimethoxy-4-(methylamino)benzonitrile (IV), and redn. of the resulting 3,5-dimethoxy-4-(dimethylamino)benzonitrile. II in MeOH was brominated with aq. HBr, the resulting III treated with MeONa/MeOH and CuCl, and the resulting IV methylated with HCO2H/paraformaldehyde followed by redn. with Raney Ni to give I.
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