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0 °C

Sodium nitrite (0.405 g, 5.88 mmol) was added to a solution of 1-benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-ethanone (1.0 g, 3.92 mmol; see Example 3B above) in a mixture of HOAc/THF/H2O (6:4:1, 22 mL). The mixture was stirred at 0° C. for 1 hour and then at room temperature for 1 hour. Solvent was removed under reduced pressure. Residue was dissolved in water and NaOH (3N) was added until the pH value was more than 8. The aqueous solution was then extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 0.90 g (81%) of 1-Benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)ethane-1,2-dione 2-oxime as a yellow foam. MS (ESP+) m/z 285.1 (M+1). 1H NMR (300 MHz, CDCl3) δ 7.49 (m, 4H), 7.09 (d, 1H, J=7.5 Hz), 6.81 (d, 1H, J=7.8 Hz), 6.04 (s, 2H), 2.43 (s, 3H).

1. waitat room temperature for 1 hour
2. customSolvent was removed under reduced pressure
3. dissolutionResidue was dissolved in water
4. additionNaOH (3N) was added until the pH value
5. extractionThe aqueous solution was then extracted with ethyl acetate
6. washThe organic layer was washed with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated