AN UNUSUALLY FACILE ANILIDE ETHANOLYSIS

Refluxing ethanol promptly converts the 2-methyl-1,3(2H,4H)-dioxoisoquinoline-4-carboxanilides (Ia-e) into ethyl 2-methyl-1,3(2H,4H)-dioxoisoquinoline-4-carboxylate (II) in good yields. The facility with which this ethanolysis occurs appears to be related to the higher energy state of I relative to II. Lack of enol character of I, presumably due to steric hindrance, and the hydrogen-bonded stabilization of its enolate anion (V) impart substantial acidic character to this molecule, and this property provides the proton which is believed to catalyze the ethanolysis. © 1969, American Chemical Society. All rights reserved.