The Synthesis and Reactions of N-Hydroxyparacetamol (N,4'-Dihydroxyacetanilide)

Abstract

The synthesis of N-hydroxyparacetamol (N,4'-dihydroxyacetanilide) is reported where a copper complex of the hydroxamic acids as a protecting group is used. It has been shown to decompose between pH 7 and 12 to give products which are derived from N-acetyl-p-benzoquinone imine.3'-Substituted 4'-hydroxyacetanilides are formed when a nucieophile is present. The properties of N-hydroxyparacetamol are consistent with it being the toxic, reactive intermediate involved in the hepatoxicity of paracetamol.