p-Toluenesulfonic acid → 1-(3-nitrophenyl)-1H-pyrrole

Participants

Reaction Steps

A mixture of 3-nitroaniline (15 g, 0.11 mmol), 2,5-dimethoxytetrahydrofuran (42 ml, 0.33 mol) and a catalytic amount of pTSA in dry toluene (150 ml) is heated to reflux for 2 hours. After cooling the mixture is concentrated under reduced pressure and the residue is purified by column-chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (1:1) as the eluent. Yield: 16 g (78%). Mp 65-70° C.

Provenance & Evidence