Sodium Hydroxide → 2-(6-Chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime

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Reaction Steps

To a solution of 2-(6-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone (74.9 g, 299.8 mmol) in methanol (900 mL) was added hydroxylamine hydrochloride (104 g, 1.49 mol) followed by sodium hydroxide (600 mL, 10% aqueous, 1.5 mol). The resultant suspension was heated to reflux for 2 hours and then cooled to room temperature. The mixture was concentrated in vacuo and the residue taken up in ether and water. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration gave a solid residue which was purified by recrystallization from ethyl acetate-hexanes to provide 2-(6-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime (67.9 g, 86%) as a white solid. 1H NMR (CDCl3): δ 8.69 (s, 1H), 7.71 (dd, 2H), 7.53 (t, 1H), 7.18–7.16 (m, 2H), 7.03 (t, 2H), 4.37 (s, 2H); 19F NMR (CDCl3δ−111.77; MS m/z 265 (M+1).

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