Process for 4-dimethylamino-3,5-dimethoxybenzaldehyde
AssigneeHoffman-La Roche Inc.
InventorsSiro Serafini, Giuseppe Zagotto
Life of this patent
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Abstract
4-Dimethylamino-3,5-dimethoxy-benzaldehyde, an intermediate for the preparation of the antibacterially active aditoprim (4-dimethylamino-3,5-dimethoxybenzoldehyde) a known antibacterially active compound, is obtained from 4-dimethylaminobenzonitrile by bromination or chlorination, replacement of the halogen by the methoxy group and reduction of the nitrile group.
Claims6
A process for the preparation of 4-dimethylamino-3,5-dimethoxybenzaldehyde, which comprises:
- (a) converting 4-dimethylaminobenzonitrile into 3,5-dibromo-(or dichloro-)4-methylaminobenzonitrile by treatment with bromine or chlorine;
- (b) converting 3,5-dibromo-(or dichloro-)-4-methylaminobenzonitrile, the reaction product of step (a) into 3,5-dimethoxy-4-methylaminobenzonitrile by treating said reaction product with an alkali methoxide in the presence of copper and dimethylformamide or dimethylacetamide;
- and
- (c) methylating 3,5-dimethoxy-4-methylaminobenzonitrile, the reaction product of step (b) to 4-dimethylamino-3,5-dimethoxybenzonitrile and reducing the latter to 4-dimethylamino-3,5-dimethoxybenzaldehyde.
A compound of the formula 3,5-dibromo-4-methylaminobenzonitrile.
A compound of the formula 3,5-dichloro-4-methylaminobenzonitrile
A compound of the formula 3,5-dimethoxy-4-methylaminobenzonitrile.
Dependencies are inferred from the claim text.