Abstract
The Friedel-Crafts acetylation of N-acetyl-o-toluidine (2) with acetyl chloride-aluminium chloride with and without carbon disulfide has been reported to give 4-acetamino-3-methylacetophenone (3) and 3-acetamino-4-methylacetophenone (5), respectively, as the main products. Reexamination of these reactions revealed that a 1 : 4.6 mixture of (3) and (5) was obtained in good yield in both cases.
The temperature and solvent dependences of this reaction were also examined. The maximum total yield (90%) of (3) and (5) was observed at 80°C without solvent. The products ratio (3) / (5) was found to be 1/4.54.9 in most runs.
