An efficient method for hydrolysis of N-monosubstituted amides utilization of intramolecular N---O acyl migration in hydroxypivalimides

Article abstract of DOI:10.1016/S0040-4020(01)86433-4

An efficient and versatile method for the hydrolysis of N-monosubstituted carboxamides has been developed. The method consists of two steps: the conversion to acetoxypivalimides (≥90% yield) and their mild alkaline hydrolysis (70 90% yield). No epimerization at the α-position of the acyl group took place in the process. The amine part of the original amides can be recovered in good yield.