Ethanol → Ethyl 5-amino-1H-indole-2-carboxylate

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Reaction Steps

A mixture of ethyl 5-nitro-1H-indole-2-carboxylate (15.0 g, 0.0641 mol), 10% palladium-on-carbon catalyst, ethanol (300 ml) and tetrahydrofuran (300 ml) is hydrogenated at an initial pressure of 47 p.s.i. for 9 h and filtered through celite. The filtrate is concentrated and the residue is digested with hot diethyl ether. Concentration of the ether extract gave the titled product (11.14 g): MS (ES) m/z 205 (M+H+), 227 (M+Na+). *Uhlig, F.; Snyder, H. R. Adv. Org. Chem. 1960, 1, 35; Parmerter, S. M.; Cook, A. G.; Dixon, W. B. J. Am. Chem. Soc. 1958, 80, 4621-2.

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