Hydrochloric Acid → alpha-Amino-7-ethyl-1H-indole-3-acetic Acid Ethyl Ester

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Reaction Steps

To 7-ethyl-α-(hydroxyimino)-1H-indole-3-acetic acid ethyl ester 5 (7.3 g, 0.028 mol) in ethanol (200 mL) was added concentrated HCl (3 mL) and 10% Pd/C (1.0 g). The mixture was hydrogenated at 40 p.s.i. for 4 hours at 22° C. The catalyst and the solvent were removed and the residue was dissolved in water. After washing with methylene chloride, the aqueous phase was basified with 20% sodium hydroxide. The precipitated product, α-amino-7-ethyl-1H-indole-3-acetic acid ethyl ester 6 (6.0 g, 87%), was filtered, washed with water and dried. A sample recrystallized from hot ethanol had m.p. 120°-122° C.

Provenance & Evidence