Hydrolysis of acyl derivatives of malonaldehyde dianil. III.

Abstract

The reaction sequence of hydrolysis of N-acyl derivatives of malonaldehyde dianil was examined. Hydrochloric acid-catalyzed hydrolysis occurred at the imino group to form arylamine and β-(N-acylarylamino) acrolein ; the latter compound is not stable in acidic solution. In the case of 1-(N-phenylcarbamoyl-p-methylphenylamino)-3-(p-methylphenylimino)-1-propene, hydrolysis occurred at both the imino and carbamoyl groups. Buffer-catalyzed hydrolysis occurred at the imino group, and the resulting β-(N-acylarylamino) acrolein and arylamine reacted to form β-arylaminoacrolein and N-acylarylamine. This aminolysis reaction was suppressed in hydrochloric acid-catalyzed hydrolysis. Alkaline hydrolysis of N-acyl derivatives of malonaldehyde dianil and of β-arylaminoacrolein occurred at the amide carbonyl group except in the case of 1-(N-tosyl-p-methylphenylamino)-3-(p-methylphenylimino)-1-propene. N-Tosyl-p-toluidine was obtained in this case.