Chemistry of Salicylic Acid and Anthranilic Acid. I. Reduction of Methyl Salicylate, Methyl Anthranilate and Their Derivatives with Sodium Borohydride

Abstract

The ester derivatives of salicylic acid and some kinds of anthranilic acid were reduced to corresponding alcohols with sodium borohydride. The reduction behavior of 4-oxo-1, 3-benzodioxanes (IXa-b), 1, 2-dihydro-4-oxo-3, 1-benzoxazines (XIIa-c, e, k) and 4-oxo-3, 1-benzoxazines (XVd-j) were also investigated. These results may be explained in terms of the contribution of the electronic structure of carbonyl group or the neighbouring participation of hydroxyl or amino group.