PYRROLE CHEMISTRY: I. SUBSTITUTION REACTIONS OF 1-METHYLPYRROLE

Abstract

An investigation of some substitution reactions of 1-methylpyrrole has indicated that the α-directing effect of the hetero nitrogen during nitration is even less than it is in pyrrole. 3-Nitro-1-methylpyrrole has been prepared together with the 2-isomer by direct nitration of 1-methylpyrrole as well as indirectly. These two compounds have been found to undergo Friedel-Crafts acylation, a reaction not previously reported among simple nitro compounds of the 5-membered heterocycles. It has been found, contrary to the results of previous workers, that direct nitration of pyrrole itself yields a mononitro product containing about 7% of the 3-isomer.