The reaction between ethyl 3-bromopyruvate and p-substituted anilines
was found to involve the unexpected participation of acetone (solvent)
forming N-aryl-5-methyl-pyrrole-3-carboxylates. The influence of p-su
bstituents of aniline and the feasibility with other ketones were stud
ied. N-aryl-indole-3-carboxylate (17) was synthesized successfully wit
h this method. The unique character of p-methoxy-aniline in this react
ion was discussed.