Dimethylformamide → 1H-Indole-6-carboxamide, N-(cyclopentylmethyl)-3-formyl-

Participants

Reaction Steps

N,N-Dimethylformamide (DMF)(20 ml) was cooled to 0° under an atmosphere of nitrogen and treated cautiously with phosphorus oxychloride (6.6 ml). This solution was stirred at 0° for 15 minutes, warmed to room temperature, and treated with a solution of 6-(N-cyclopentylmethylcarbamoyl)indole (14.3 g) in DMF (100 ml). The yellow mixture was stirred for 2 hours and then brought to pH 14 by the addition of ice and 20% (w/v) aqueous sodium hydroxide. The mixture was heated to reflux for 5 minutes and allowed to cool. The precipitate which formed was collected by filtration and triturated with ether to give 6-(N-cyclopentylmethylcarbamoyl)-3-formylindole (9.6 g, 60%) as a tan powder; mp 224°-225°.

Provenance & Evidence