Oxygen → 4-(4-Methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

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Reaction Steps

A mixture of potassium tert-butoxide (5.54 g, 49.3 mmol) in DMSO (20 mL) was added to a mixture of (E)-3-(4-methoxyphenyl)acrylaldehyde (2.0 g, 12.33 mmol) and 2-cyanoacetamide (1.140 g, 13.56 mmol) in DMSO (30 mL) dropwise under an oxygen balloon with a water bath cooling outside. After completion of addition, the mixture was stirred under oxygen for 1 h at room temperature, quenched with water (100 mL) and adjusted to pH 5-6 with careful addition of 1 N HCl. A brown precipitate was formed, collected by filtration, washed with water (2×50 mL), dried under vacuum to give 4-(4-methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile (1.0 g, 36% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.69 (1H, δ, J=6.60 Hz), 7.62 (2H, δ, J=8.80 Hz), 7.11 (2H, δ, J=8.80 Hz), 639 (1H, δ, J=6.60 Hz), 3.87 (3H, s); MS (ES+) m/z: 227 (M+H); LC retention time: 2.532 min (analytical HPLC Method A).

Provenance & Evidence