Aluminum → Ethyl 2-amino-2-cyanoacetate

Participants

Reaction Steps

To aluminum foil (25 g) was added a solution of mercury(II) chloride (10 g, 0.37 mol) in water (1 L). The mixture was swirled for 5 min, and then the turbid solution was decanted off. The resulting aluminum amalgam was washed successively with water, methanol and diethyl ether. To amalgam suspended in diethyl ether (500 mL) at 0° C., was added a solution of ethyl 2-hydroxyimino-2-cyanoacetate (100 g, 0.70 mol) in diethyl ether (300 mL), followed by water (50 mL), maintaining a gentle reflux. After 1 h of stirring, the mixture was filtered and the filtrate was washed with water, brine and dried (Na2SO4). Removal of the solvent gave the title compound as a white solid (67 g, 74%). 1H NMR (250 MHz, CD3OD) δ 4.45 (m, 2H), 2.49 (s, 1H), 1.38 (m, 3H).

Provenance & Evidence