Quinone → HCID 131713950, compound

Participants

Reaction Steps

A solution of 0.334 g of ethyl β-(3-pyridyl)-β-(5-ethoxycarbonylpentylamino)acrylate and 0.108 g of p-benzoquinone in 1 ml of glacial acetic (according to the general procedure as described in J. Chem. Soc. C 1968, 1795) is heated at 60° for 4 hours. The reaction mixture is cooled, diluted with 10 ml of water, neutralized to pH 7 with saturated sodium bicarbonate solution and extracted with methylene chloride. The methylene chloride extract is dried, evaporated to dryness and the resulting product is purified by preparative TLC (silica gel; ethyl acetate, hexane 1:1) to give 1-(5-ethoxycarbonylpentyl-3-ethoxycarbonyl-5-hydroxy-2-(3-pyridyl)indole, NMR δ3.95, 4.1, 8.75.

Provenance & Evidence