Hydrochloric Acid → 2-Chloro-5-methylpyridin-1-ium-1-olate

Temperature

0 °C

Into a mixture of 2-chloro-5-methylpyridine (27.4 g, 215 mmol), urea hydrogen peroxide addition compound (42.5 g, 452 mmol), dichloromethane (250 ml) was added dropwise anhydrous trifluoroacetic acid (60.7 ml and 430 mmol) at 0° C., and the reaction mixture was stirred at 0° C. for 1 hour. Then, after stirring for 45 minutes while elevating the reaction temperature to room temperature, an aqueous solution (450 ml) of sodium hydrosulfite (45 g) was added, and the reaction mixture was stirred for 15 minutes. 0.5N hydrochloric acid (400 ml) was added and the mixture was extracted with dichloromethane (400 ml), and after washed with sodium bicarbonate solution, the mixture was dried over magnesium sulfate and the solvent was evaporated, thereby yielding the title compound (22.5 g, 157 mmol, 73%) as a beige solid.

1. stirringThen, after stirring for 45 minutes
2. customto room temperature
3. stirringthe reaction mixture was stirred for 15 minutes
4. extractionthe mixture was extracted with dichloromethane (400 ml)
5. washafter washed with sodium bicarbonate solution
6. dry with materialthe mixture was dried over magnesium sulfate
7. customthe solvent was evaporated

ORD record

ord-396e50224dea4a7b805a24e8eddbdf4d

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07781452B2