Cyanoacetamide → 5-Cyclopropyl-6-ethyl-1,2-dihydro-2-oxo-3-pyridinecarbonitrile

Participants

Reaction Steps

A sample of 2-Cyclopropyl-1-(morpholin-4-yl)pent-1-en-3-one (2A, 2.09 g, 10 mmol), cyanoacetamide (0.92 g, 11 mmol) and piperidine acetate (4 mL) were dissolved in ethanol (30 mL) under nitrogen. The reaction mixture was heated at reflux for 24 hours. The reaction mixture was cooled and concentrated, then diluted with methylene chloride. The solution was washed with brine and dried (MgSO4), filtered and concentrated. The crude solid was chromatographed (silica, 5% methanol/methylene chloride) to afford pure title compound (3A, 1.54 g, 82%) as a crystalline solid. 1H NMR (300 MHz, CDCl3): δ0.62 (m, 2H), 0.98 (m, 2H), 1.38 (t, 3H), 1.71 (m, 1H), 2.91 (q, 2H), 7.63 (s, 1H); MS (DCI/NH3) m/e 189 (M+H)+, 206 (M+NH4)+. Anal. Calcd for C11 H12N2O: C, 70.19; H, 6.42; N, 14.88. Found C, 70.31; H, 6.49; N, 14.62.

Provenance & Evidence