Hydrochloric Acid → 6-Methyl-2-oxo-4-propyl-1,2-dihydropyridine-3-carbonitrile

Participants

Reaction Steps

To a stirred solution of t-BuOK (20 g, 178.5 mmol) and cyanoacetamide (16.5 g, 196 mmol) in DMSO (300 mL) was added (3E)-3-hepten-2-one (20 g, 178.3 mmol) under argon atmosphere at room temperature. The reaction mixture was stirred at room temperature for 30 min and then additional t-BuOK (60 g, 535.7 mmol) was added to the reaction mixture. The argon was then displaced by oxygen gas and stirred for 48 hrs at room temperature under oxygen. Reaction mixture was cooled to 0° C. and diluted with water (80 mL) followed by 4N HCl (120 mL). The mixture was stirred for 15 min and the solid was filtered. The solid was washed with water (1 L) and dried to afford 1,2-dihydro-6-methyl-2-oxo-4-propylpyridine-3-carbonitrile as an off white solid (12 g, 38%). 1H NMR (CDCl3, 400 MHz): δ 1.030 (t, 3H, J=7.2 Hz), 1.728 (m, 2H), 2.429 (s, 3H), 2.701 (t, 2H, J=7.6 Hz), 6.083 (s, 1H). LCMS E-S (M−H)=175.11.

Provenance & Evidence