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
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=2)=[CH:4][C:3]=1[NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21]>C(O)(=O)C>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])[CH:4]=2)=[N:10][CH:11]=1Participants
3
Conditions
- Temperature
- 60 °C
Procedure
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.