Fries rearrangement of acetanilide over zeolite catalysts

Zeolites Y and Beta have been evaluated for the Fries type rearrangement of acetanilide (1) to the corresponding aminoacetophenones. Aniline was the major product but in the presence of added acetic anhydride the major product was meta-aminoacetophenone (3). The photo-Fries rearrangement was attempted for X, Y and Beta zeolites impregnated with 1. In contrast to the catalytic rearrangement at elevated temperatures the major product was the ortho-aminoacetophenone (2). It appears that the selectivity for the ortho isomer improves at the expense of conversion with decreasing acidity. (C) 1998 Elsevier Science B.V. All rights reserved.