Intramolecular aminolysis of amides. The cyclization of 2-aminomethylbenzamide to phthalimidine

TH Fife, BR DeMark

Index: Fife,T.H.; DeMark,B.R. Journal of the American Chemical Society, 1977 , vol. 99, p. 3075 - 3080

Full Text: HTML

Citation Number: 15

Abstract

Abstract: Rate constants for cyclization of 2-aminomethylbenzamide to phthalimidine have been determined in HzO at 30 OC and p= 0.5. Hydroxide ion catalysis takes place at high pH with koH= 0.16 M-'sI, which is approximately the same as koH for cyclization of 2- hydroxymethylbenzamide to phthalide but 104-fold less than ko~ for cyclization of methyl 2- aminomethylbenzoate to phthalimidine. Thus, as in the case of aliphatic esters, the rate ...