Hydrolytic Behavior of N-Acyl Phthalimides

Abstract

The hydrolysis of N-acyl phthalimides was studied to determine the effect of the N-acyl moiety on the hydrolytic rate and hydrolytic products, i.e., whether hydrolysis leads to the regeneration of the parent phthalimide or to formation of the corresponding N-acyl phthalamic acid. A series of N-acyl phthalimides was prepared and their hydrolysis was observed in the neutral to alkaline pH range at 25°. It was found that N-acetyl-, N-propionyl-, N- (ethoxycarbonyl)-, and W-(morpholinocarbonyl)phthalimides gave their corresponding N-acyl phthalamic acid as their major hydrolytic product while N-chloroacetyl- and N-bromoacetylphthalimides gave phthalamide and the corresponding carboxylic acid. The change in path depending on the N-acyl group was rationalized in terms of the susceptibility of the appropriate carbonyls to attack. The hydrolysis of N-acyl phthalimides was studied to determine the effect of the N-acyl moiety on the hydrolytic rate and hydrolytic products, i.e., whether hydrolysis leads to the regeneration of the parent phthalimide or to formation of the corresponding N-acyl phthalamic acid. A series of N-acyl phthalimides was prepared and their hydrolysis was observed in the neutral to alkaline pH range at 25°. It was found that N-acetyl-, N-propionyl-, N- (ethoxycarbonyl)-, and W-(morpholinocarbonyl)phthalimides gave their corresponding N-acyl phthalamic acid as their major hydrolytic product while N-chloroacetyl- and N-bromoacetylphthalimides gave phthalamide and the corresponding carboxylic acid. The change in path depending on the N-acyl group was rationalized in terms of the susceptibility of the appropriate carbonyls to attack.