Hydrochloric Acid → 2-Chloro-4-methoxypyridin-3-amine

To a solution of 6.4 g (51 mmol) of 3-amino-4-methoxypyridine in 30 mL of 37 percent aqueous hydrochloric acid was slowly added 7.8 g of 30 percent aqueous hydrogen peroxide at room temperature with stirring. After 30 min this solution was slowly poured into 300 mL of saturated aqueous sodium bicarbonate and the resulting mixture was extracted with ether (3×200mL). The ethereal extracts were combined, dried over magnesium sulfate, and filtered, The fittrate was concentrated by evaporation under reduced pressure to obtain a light brown solid. This solid was purified by column chromatography (17:83 acetone:hexane) to obtain 6.54 g (81 percent of theory) of the title compound as colorless needles melting at 86°-87° C.

1. customat room temperature
2. extractionthe resulting mixture was extracted with ether (3×200mL)
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationThe fittrate was concentrated by evaporation under reduced pressure
6. customto obtain a light brown solid
7. customThis solid was purified by column chromatography (17:83 acetone:hexane)

ORD record

ord-7a8e65fdd66d44d9bf8b58015ae3de71

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05614469