High-Pressure Aminolysis of Lactones to Hydroxy Amides.

The preparation of hydroxy amides from a wide variety of lactones and amines has been achieved at 9 kbar and 30 or 65 °C. The yields of hydroxy amides were moderate to excellent. Some limitations were encountered in the reaction of 6-hexanolide; for example, diethylamine gave only a 15% yield of the corresponding amide at 8 kbar and 60 °C. 4-Pentanolide did react with extremely unreactive amines such as 4-nitroaniline and diphenylamine, and the product was a mixture of the hydroxy amide and 3-aminobutyric acid.