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 filtrate 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 filtrate 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-71d869eba95c481899397e10f14b2ff3

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05461161