Nitrogen → HCID 12147024, compound

Participants

Reaction Steps

To a stirred slurry of 1-[(2-ethoxycarbonyl)ethyl]-3-hydroxy-6-methylpyrazinone (2-6) (3.8 g, 16.8 mmol) in 20 mL of dichloromethane, phosphorous oxybromide (5.8 g, 20.2 mmol) was added at 50° C. under a steady stream of N2. The resulting mixture was stirred for 2 hours. The reaction mixture was allowed to cool to room temperature and stirring was continued overnight. The mixture was diluted with 30 mL of chloroform and 30 mL of cold water, basified with ammonium hydroxide, and extracted with 30 mL of chloroform (3×). The combined organic layers were dried over anhydrous sodium sulfate, and concentrated in vacuo to yield the title compound (3.8 g, 80%) as an orange solid; the product was verified by NMR. 1H NMR (CDCl3): δ 7.01 (s, 1H), 4.26 (q, 2H), 4.16 (q, 2H), 2.83 (t, 2H), 2.38 (s, 3H), 1.25 (t, 3H).

Provenance & Evidence