Sodium Hydroxide → 2-(4-Chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone oxime

Participants

Reaction Steps

To a solution of 2-(4-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone in methanol (200 mL) was added hydroxylamine hydrochloride (27.2 g, 392 mmol) followed by the addition of a sodium hydroxide solution (15.7 g, 392 mmol in 50 mL of water). The resulting suspension was heated at reflux for 1 hour and then allowed to cool to room temperature. The mixture was concentrated and water was added to the resulting slurry. A white precipitate formed, which was collected by filtration, washed with water and dried to give 2-(4-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone oxime (11.8 g) as a white solid. 1H NMR (CDCl3): δ 8.47 (d, 1H), 7.72 (d, 2H), 7.36 (d, 1H), 7.19 (dd, 1H), 6.91 (d, 2H), 4.43 (s, 2H), 3.84 (s, 3H); MS m/z 277 (M+1).

Provenance & Evidence