STUDIES IN THE POLYOXYPHENOL SERIES: IV. THE SYNTHESIS OF N-ETHYL-3,4-DIMETHOXYANILINE FROM GUAIACOL

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Abstract
N-Ethyl-3,4-dimethoxyaniline (N-ethyl-4-aminoveratrole) was prepared in 50% to 60% yield by heating 4-bromoveratrole with aqueous ethylamine and a cuprous chloride catalyst at 95° to 100 °C. This synthesis was much better than those previously reported. Replacement of the ethylamine with ammonia yielded only 33% of crystalline 4-aminoveratrole, which others have shown to be much more readily accessible from the 4-nitro derivative. Some of the published methods of preparing 4-bromoveratrole from guaiacol were compared, and the compound was also obtained by the direct bromination of veratrole. The acetate of 4-bromoveratrole, m.p. 49 °C., and 3,4-dimethoxyformanilide, m.p. 88 °C., were described, apparently for the first time.

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