Hydroxyamine hydrochloride → ethyl 3-[5-[(Z)-N'-hydroxycarbamimidoyl]indol-1-yl]propanoate

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-(5-cyano-1H-indol-1-yl)propanoate (D51) (1.7 g, 7.2 mmol), hydroxylamine hydrochloride (1.0 g, 14.4 mmol) and sodium hydrogen carbonate (2.42 g, 28.9 mmol) were suspended in ethanol (100 ml) and stirred at 50° C. for 3 days. A single product formed but 15% starting material remained. Cooled, filtered off the inorganic material and evaporated off the solvent. The product was crystallised from a mixture of EtOAc, diethyl ether and hexane to yield 1.9 g of the title compound as a white solid. MS (ES) C14H17N3O3 requires 275; found 276. (MH+).

Provenance & Evidence