Methanol → 6-(4-Chlorophenyl)-5-(phenyl)-2-oxo-1,2-dihydropyridine-3-nitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 3-dimethylamino-1-(4-chlorophenyl)-2-(phenyl)prop-2-en-1-one (43.3 mmol assumed) from Step A, cyanoacetamide (4.0 g, 47.6 mmol), and methanol (3.9 mL, 95 mmol) in DMF (100 mL) was added dropwise to a suspension of sodium hydride (60% in mineral oil) (4.3 g, 108 mmol) in DMF (50 mL) at rt. After the slow addition was complete, the reaction was heated to 95° C. for 2 h. Most of the DMF was then removed in vacuo before the reaction was diluted with aqueous 18% citric acid solution. The mixture was extracted twice with methylene chloride and the organic layers were washed with a portion of brine. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The solid residue was triturated with ether, filtered, and air dried to afford 6-(4-chlorophenyl)-5-(phenyl)-2-oxo-1,2-dihydropyridine-3-nitrile. HPLC/MS: 307 (M+1); Rt=3.0 min;

Provenance & Evidence