The reactions of phenols with phthalodinitrile and 3-amino-1H-isoindoles

Abstract

Phenols react with phthalodinitrile, alone or catalysed by hydrogen chloride to give 2-amino-1,1-di(hydroxyaryl)-1H-isoindoles. The hydrogen chloride-catalysed reaction of para-cresol is anomalous. These amino-1H-isoindoles react further with phenols with the liberation of ammonia and the formation of 1,3,3-tri(hydroxyaryl)-1H-isoindoles and other, tarry, products. A related reaction occurs between phenols and 3-amino-1H-isoindolone.