The reaction of 3-hydroxy-2-naphthanilide with chloro-s-triazines

Abstract

N.m.r., i.r. data, and chemical behaviour support the view that ionised 3-hydroxy-2-naphthanilide reacts with cyanuric chloride and with dichloro-s-triazines to form initially the O-s-triazinyl derivatives (3). These hydrolyse in acid to 3-hydroxy-2-naphthanilide; in the presence of alkali, however, O→N rearrangement of the s-triazine occurs to give the N-s-triazinyl derivatives (5) which hydrolyse to 3-hydroxy-2-naphthoic acid.