Hydrochloric Acid → HCID 12805221, compound

Participants

Reaction Steps

A solution of 3-[2-(1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-acetic acid (0.2 g) and triethylamine (0.061 g) in chloroform (10 ml) was treated with isobutylchloroformate (0.08 g) at -5°, resulting red solution stirred at the same temperature for 20 h and cyclohexylamine was added to the resulting anhydride (0.06 g). Reaction was allowed to warm up to ambient temperature and stirred for 1 h then the mixture was poured into dilute hydrochloric acid (2N, 20 ml) extracted with chloroform (3×10 ml), dried (MgSO4), solvent removed and residual oil purified by chromatography (silica Merck, 7734; 10 g; 1% methanol in dichloromethane as eluent). Product was obtained as an oil which on treatment with ethyl acetate/ether gave the title compound as a solid (0.09 g) m.p. 175°-6°.

Provenance & Evidence