Effect of Substituted Pyridines and Aliphatic Tertiary Amines on the Benzoylation of Benzanilide

Abstract

The coexistence of pyridine and triethylamine promotes the benzoylation of benzanilide. The effect of basicity and steric hindrance of substituted pyridines and aliphatic tertiary amines on the ease of the benzoylation has now been studied by high pressure liquid chromatography. More basic pyridine, if not sterically hindered, was found to be effective in promoting the benzoylation when the pK_a of the conjugate acid of the coexistent aliphatic tertiary amine was higher than about 8.