Water → N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]benzamide

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Reaction Steps

A stirred mixture, under N2, of 24.6 g of 1-(2-aminophenyl)indoline hydrochloride in 225 ml of dry CH2Cl2 is treated with 20.2 g of triethylamine over 10 minutes. The mixture is cooled to 0°-5° C., and kept at that temperature while a solution of 14.1 g of benzoyl chloride and 25 ml of CH2Cl2 is added dropwise over 1.0 hour. After stirring at room temperature overnight, H2O was added and the layers are separated. The organic phase is washed further with H2O, 3 N--HCl, 3 N--NaOH, again with H2O, and dried. The solvent is removed to leave an oil which crystallizes on standing to yield 1-(2-benzamidophenyl)indoline, m.p. 73°-76° C.

Provenance & Evidence