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

To a magnetically stirred mixture of 3-Amino-4-methoxypyridine (4.45 g, 35.89 mmole) in 12N HCl (25 mL) cooled in an ice bath was added hydrogen peroxide (5.3 g, 46.65 mmol, 30% solution). The reaction was allowed to slowly warm to room temperature and stirred for 1 h. TLC (50% ethyl acetate/hexane) indicated complete consumption of starting material. The reaction mixture was slowly poured into saturated sodium bicarbonate solution (400 mL) to neutralize the reaction and extracted with ethyl acetate. The resulting organic layers were washed with saturated sodium chloride solution and dried over magnesium sulfate. Filtration and concentration gave 3-Amino-2-chloro-4 methoxypyridine (4.56 g, 28.77 mmol, 80% yield) as an orange solid.

1. temperaturecooled in an ice bath
2. customconsumption of starting material
3. additionThe reaction mixture was slowly poured into saturated sodium bicarbonate solution (400 mL)
4. customthe reaction
5. extractionextracted with ethyl acetate
6. washThe resulting organic layers were washed with saturated sodium chloride solution
7. dry with materialdried over magnesium sulfate
8. filtrationFiltration and concentration

ORD record

ord-2548548e228445b1832b59a62bec1785

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947692B2