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 concentrate was diluted with ethyl acetate (150 mL), aqueous sodium hydrogen carbonate solution (200 mL) was gradually added, and the mixture was filtered through celite. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residual oily substance was dissolved in toluene, and purified by silica gel column chromatography (ethyl acetate/hexane=20/80→80/20) to give the title compound (10.9 g, 91%) as a brownish-red oil.

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

ORD record

ord-2f6dc9dc132e422b9cdac93cfbd3a16b

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697874B2