N-{2-chloro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide → N-{5-[(5-aminopyridin-2-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide

Temperature

60 °C

N-{2-Chloro-5-[(5-nitropyridin-2-yl)oxy]phenyl}-2,2,2-trifluoroacetamide (13 g, 35.9 mmol) was dissolved in acetic acid (200 mL), reduced iron (10 g, 179 mmol) was added, and the mixture was stirred at 60° C. for 3 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The concentrated solution was diluted with ethyl acetate (150 mL), aqueous sodium hydrogen carbonate solution (200 mL) was slowly added, and the mixture was filtered through celite. The organic layer was collected, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residual oil was dissolved in toluene, and the solution was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→20/80) to give the title compound (10.9 g, 91%) as a brown oil.

1. temperatureAfter cooling to room temperature
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. additionThe concentrated solution was diluted with ethyl acetate (150 mL), aqueous sodium hydrogen carbonate solution (200 mL)
4. additionwas slowly added
5. filtrationthe mixture was filtered through celite
6. customThe organic layer was collected
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. dissolutionThe residual oil was dissolved in toluene
10. customthe solution was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→20/80)

ORD record

ord-34fd6363ff10410d9f057b02d0127d0b

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2