Hydrogen Peroxide → 2-Chloro-6-methylpyridine 1-oxide

Temperature

87.5 °C

30% Hydrogen peroxide solution (20 mL, 0.176 mol) was added slowly into a solution of 2-chloro-6-methylpyridine (5.0 g, 39.4 mmol) in glacial acetic acid (30 mL) whilst the mixture was kept below 20° C. The reaction mixture was then heated to 85-90° C. overnight. The reaction was cooled and neutralised with cold sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane (4×50 mL) and the combined organic layers washed with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford 2-chloro-6-methyl-pyridine-1-oxide (5.43 g, 96.5%) as an oil.

1. customwas kept below 20° C
2. temperatureThe reaction was cooled
3. extractionThe aqueous layer was extracted with dichloromethane (4×50 mL)
4. washthe combined organic layers washed with water (50 mL) and brine (50 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-a0b4789d56274b6dba9f24e97b13ceea

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604029B2