Pyridine-2-carbonitrile → 3,4-Dimethoxyphenyl 2-pyridyl ketone

Participants

Reaction Steps

2-(3,4-Dimethoxybenzoyl)pyridine was prepared analogously to 4-(3,4-dimethoxybenzoyl)pyridine using 2-cyanopyridine. The crude mixture was purified by flash column chromatography (silica gel, 1% methanol/methylene chloride) to afford after drying in vacuo (60° C., 1 mm) 1.67 g (34%) of the product: mp 91.5-93° C.; 1H NMR (CDCl3) δ 8.76-8.70 (m, 1H), 8.05-7.71 (m, 4H), 7.55-7.45 (m, 1H), 7.00-6.89 (m, 1H), 3.96 (s, 3H), 3.96 (s, 3H); 13C NMR (CDCl3) δ 192.1, 155.7, 153.3, 148.7, 148.2, 136.9, 128.9, 126.7, 125.7, 124.4, 112.6, 109.8, 56.0, 55.9; Anal. Calcd for C14H13NO3. Theoretical: C, 69.12; H, 5.39; N, 5.76. Found: C, 68.96; H, 5.47; N, 5.66.

Provenance & Evidence