Ethyl 3-aminobenzoate → 1-(3-Ethoxycarbonylphenyl)pyrrole

Participants

Reaction Steps

Ethyl m-aminobenzoate (1.6 g) was dissolved in 10 ml of glacial acetic acid, and 1.3 g of 2,5-dimethoxytetrahydrofuran was added. The mixture was refluxed for 2 hours, and the solvent was evaporated. The residue was dissolved in a mixture of ethyl acetate and water. The organic layer was separated, and then worked up in a customary manner. Finally, recrystallization from hexane gave 1.7 g (yield 82%) of ethyl 3-(1-pyrrolyl)benzoate as colorless needles having a melting point of 64° to 65° C. The resulting pyrrolyl compound (1.1 g) was dissolved in 30 ml of ethyl ether, and with stirring under ice cooling, 0.2 g of lithium aluminum hydride was added. The mixture was stirred for 1 hour. The reaction mixture was extracted by adding water and ethyl ether. The extract was worked up in a customary manner. Recrystallization from a mixture of ethyl acetate and hexane gave 0.80 g (yield 91%) of 3-(1-pyrrolyl)benzyl alcohol as colorless needles having a melting point of 66° to 68° C.

Provenance & Evidence