(Z)-Methyl 2-(hydroxyiMino)-2-(pyridin-2-yl)acetate

1658-42-0

154410-82-9

The general procedure for the synthesis of methyl 2-(oxime)-2-(pyridin-2-yl)acetate from methyl 2-pyridylacetate was as follows: to a stirring solution of methyl 2-pyridylacetate (8.9 mL, 0.66 mmol) in acetic acid (16 mL) at 0 °C, an aqueous sodium nitrite solution (4.67 g, 0.66 mmol, 14 mL) was slowly added. After addition, the reaction mixture was continued to be stirred at room temperature for 40 min. Subsequently, water (30 mL) was added and the mixture was stirred for another 1 hour. Upon completion of the reaction, the mixture was concentrated to remove most of the acetic acid and alkalized with aqueous sodium carbonate to pH 8-9. The aqueous phase was extracted with ethyl acetate (3×). The organic phases were combined, dried with magnesium sulfate, filtered, and concentrated under vacuum. Finally, the product was dried in a vacuum oven to afford methyl 2-(oxime)-2-(pyridin-2-yl)acetate (11.6 g, 97% yield) as an off-white solid with a mass spectrum m/z 181.6 [M + 1]+.