Sodium Hydroxide → 4-(2-Fluoropyridin-3-yl)cyclohexanone oxime

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Reaction Conditions

Reaction Steps

A suspension of aminooxysulfonic acid (0.35 g, 3.11 mmol) in 96% formic acid (2.5 mL) was added dropwise to a solution of 4-(2-fluoropyridin-3-yl)cyclohexanone (0.50 g, 2.59 mmol) in 96% formic acid (2.5 mL) at room temperature. The solution was stirred for 15 min, then warmed to 40° C. for 2 h, then cooled 0° C. Ethyl acetate (10 mL) was added and the mixture was neutralized by the dropwise addition of 10 N aqueous sodium hydroxide solution (10 mL) followed by saturated aqueous sodium bicarbonate. The resulting biphasic mixture was separated, the aqueous layer was extracted with ethyl acetate (2×), and the combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give 4-(2-fluoropyridin-3-yl)cyclohexanone oxime. [M+1]=209.1.

Provenance & Evidence