Water → Ethyl 2-amino-2-(hydroxyimino)acetate

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Reaction Steps

Water (600 ml) is added dropwise over a period of two hours to a vigorously stirred, room temperature mixture of ethyl cyanoformate (99 g, 1 mol), hydroxylamine hydrochloride (105 g, 1.5 mol ) and sodium carbonate (82 g, 0.77 mol ) in ethanol (1 L.) The resulting solution is stirred until the starting material has been consumed. When the reaction is complete, most of the solvent is removed in vacuo and the resulting residue is extracted with methylene chloride (3×200 ml.) The combined organic extracts are washed with brine (250 ml), dried (Na2SO4), filtered and concentrated to afford 120.1 g (91%) of compound 2a as a white solid. Further purification can be achieved by crystallization from chloroform and hexanes. 1H NMR (CDCl3): δ9.15 (br s, OH), 5.12 (br s, 2H), 4.32 (q, 2H), 1.42 (t, J=7.1 Hz, 3H). 13C NMR (CDCl3): δ161.4, 144.4, 62.8, 14.3.

Provenance & Evidence