Water → 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

Reduced iron (1.3 g) and ammonium chloride (2.1 g) were added to water (40 mL), and the mixture was stirred at room temperature for 5 min. A solution of 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (1.8 g) in methanol (40 mL) was added, and the mixture was stirred at room temperature for 1 hr. Reduced iron (2.3 g) was added, and the mixture was further stirred at the same temperature for 3 hr. The reaction mixture was filtered through celite, and celite was washed with ethyl acetate. The filtrate was extracted with ethyl acetate, and the extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1) to give the title compound as a solid (yield 1.0 g, 65%).

1. stirringthe mixture was stirred at room temperature for 1 hr
2. stirringthe mixture was further stirred at the same temperature for 3 hr
3. filtrationThe reaction mixture was filtered through celite, and celite
4. washwas washed with ethyl acetate
5. extractionThe filtrate was extracted with ethyl acetate
6. washthe extract was washed with saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1)

ORD record

ord-beaaae8ae52e4822ad107bbb820dca53

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299261B2