Carbazole → 9H-Carbazole-1-carbonitrile

Participants

Reaction Steps

To 5.4 ml of a solution of 2.04M of boron trichloride in toluene was added a solution of 1.67 g of carbazole in 10 ml of toluene, and the mixture was refluxed for 1 hr. After cooling, the mixture was treated with 1 ml of methyl thiocyanate and stirred at room temperature for 3 hr. The reaction mixture was poured into 4N aqueous sodium hydroxide under ice-cooling and stirred at 100° C. on an oil bath for 30 min. After cooling, the reaction solution was extracted with methylene chloride, washed with water and dried over anhydrous magnesium sulfate. The residue was chromatographed on a column of silica gel, and the eluate with methylene chloride was discarded. The eluate with 10% acetonitrile-methylene chloride was concentrated, and the product was recrystallized from acetone-ether to give 1.45 g of 1-cyanocarbazole as white crystals melting at 200°-201° C.

Provenance & Evidence