Hydrochloric Acid → 3-[3-(carboxymethylthio)propyl]-N-(3-pyridyl)indole hydrochloride

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Reaction Steps

A solution of 90 mg of 3-[3-(ethoxycarbonylmethylthio)propyl]-N-(3-pyridyl)indole in 5 ml of methanol and 1 ml of 1N sodium hydroxide is refluxed for 10 hours, cooled and evaporated. The resulting oil is partitioned between ether and water. The aqueous phase is brought to pH=6 with concentrated sulfuric acid, is extracted with chloroform and the chloroform extract is dried over sodium sulfate. Filtration and evaporation gives an oil which is redissolved in 2 ml of acetone and is treated with 0.07 ml of 3N ethereal hydrogen chloride. Evaporation and crystallization from acetone-ether yields 3-[3-(carboxymethylthio)propyl]-N-(3-pyridyl)indole hydrochloride, m.p. 106°-110°.

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