Hydrochloric Acid → HCID 60060166, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(6-Chloro-3-nitro-pyridin-2-yl)-malonic acid diethyl ester (32.45 g, 103 mmol), LiCl (16.18 g, 268 mmol), H2O (10 mL), and dimethyl sulfoxide (50 mL) is stirred at 120° C. for a period of 24 h. The mixture is cooled to room temperature and diluted with H2O (400 mL). 1 N HCl (aq.) is added until all of the solids are dissolved. The mixture is extracted with EtOAc (5×150 mL), and the combined organic extracts washed with H2O (2×100 mL), then brine (100 mL), and dried over Na2SO4. The mixture is filter to remove the solids, concentrated, and purified by flash chromatography on silica (elute with 5% EtOAc in hexanes) to give the title compound as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 8.39 (d, 1H, J=8.7 Hz), 7.47 (d, 1H, J=8.7 Hz), 4.28 (s, 2H), 4.19 (q, 2H, J=7.1 Hz), 1.27 (t, 3H, J=7.1 Hz); 13C (100 MHz, CDCl3) δ 168.7, 166.8, 154.8, 151.4, 135.9, 124.4, 61.7, 41.9, 14.3; MS (CI) m/z 255.2 (M+1).

Provenance & Evidence