Ammonium Hydroxide → 3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole

Participants

Reaction Steps

To a mixture of 10.0 g of N-(3-pyridyl)-indole (J. Chem. Soc. (C), 85, 1970) and 13.8 g of glutaric acid monoethyl ester chloride in 90 ml of methylene chloride is added dropwise over a period of 3 hours a solution of 20.1 g of stannic chloride in 60 ml of methylene chloride. The reaction mixture is stirred at room temperative overnight. The reaction mixture is cooled to 10°-15° and 150 ml of 14% aqueous ammonium hydroxide is added. The organic layer is separated, washed with water and dried over sodium sulfate to yield 3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole, melting at 95°-97°.

Provenance & Evidence