Hydrochloric Acid → 1-(p-Carboxybenzyl)-2-(1-imidazolyl)-3-methylindole

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Reaction Steps

A solution of 3-methyl-2-(1-imidazolyl)indole (1.50 g) in dimethylformamide (10 ml) is added dropwise to a suspension of 50% sodium hydride dispersion in mineral oil (0.77 g) in dimethylformamide (20 ml) stirred under nitrogen at 5°-10°. The suspension is stirred at 5°-10° for 1/2 hour. A solution of α-bromotoluic acid (1.63 g) in dimethylformamide (5 ml) is added dropwise to the suspension. The suspension is again stirred at 5°-10° for 1/2 hour and then overnight at room temperature. The suspension is diluted with water (100 ml) and acidified to pH 6 to 7 with 1N hydrochloric acid. The white precipitate which forms is collected by vacuum filtration, washed with water and dried to give 1-(p-carboxybenzyl)-2-(1-imidazolyl)-3-methylindole, m.p. 221°-5°. Recrystallization from acetonitrile gives crystals melting at 225°-7°.

Provenance & Evidence