Potassium Carbonate → HCID 73554558, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile (1.00 g, 4.42 mmol) and phosphoryl trichloride (8 mL, 87 mmol) was heated to 110° C. for 15 h. The mixture was diluted with ethyl acetate (100 mL), carefully treated with saturated sodium bicarbonate (100 mL), neutralized to pH˜7 with careful addition of solid potassium carbonate while stirring vigorously, and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine (40 mL), dried (MgSO4) and concentrated to give 2-chloro-4-(4-methoxyphenyl)nicotinonitrile as a brown solid (960 mg, 89% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.54 (1H, δ, J=5.27 Hz), 7.48-7.82 (2H, m), 7.38 (1H, δ, J=5.27 Hz), 6.94-7.18 (2H, m), 3.90 (3H, s); MS (ES+) m/z: 245 (M+H); LC retention time: 3.303 min (analytical HPLC Method A).

Provenance & Evidence