Nitrogen → 3-cyano-4-isopropyl-6-methyl-2(1H)-pyridinone

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-cyanoacetamide (35.1 g, 417 mmol) and t-BuOK (42.5 g, 379 mmol) in DMSO (631 ml) was added 5-methyl-3-hexen-2-one (50.0 ml, 379 mmol) under N2 atmosphere. The mixture was stirred at 23° C. for 30 min and then additional t-BuOK (127 g, 1137 mmol) was added. The N2 gas was displaced by O2 gas and the mixture was stirred for 45 h at 23° C. under oxygen. The mixture was cooled to 0° C., diluted with H2O (200 ml) and HCl (5N, 227 ml, slowly added). The mixture was stirred for 15 min at 0° C. and the solid was filtered with Buchner funnel. The solid was washed with H2O (1500 ml) and dried with hot-air (55° C., 16 h) to give 6-methyl-2-oxo-4-(propan-2-yl)-1,2-dihydropyridine-3-carbonitrile (26.6 g, 40% yield). 1H NMR (400 MHz, CDCl3): δ 6.14 ppm (s, 1H), 3.25-3.29 (m, 1H), 2.45 (s, 3H), 1.26 (d, J=6.8 Hz, 6H); LC-MS: m/z 177.1 [M+1], 198.9 [M+23].

Provenance & Evidence