3-(Difluoromethoxy)-2-nitropyridine → 3-(Difluoromethoxy)pyridin-2-amine
Reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[C:5]([N+:10]([O-])=O)=[N:6][CH:7]=[CH:8][CH:9]=1>C(O)C.C(O)(=O)C>[F:13][CH:2]([F:1])[O:3][C:4]1[C:5]([NH2:10])=[N:6][CH:7]=[CH:8][CH:9]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
[step 2] 3-(Difluoromethoxy)-2-nitropyridine (450 mg, 2.37 mmol) obtained in step 1 was dissolved in ethanol (2 mL)-acetic acid (2 mL), reduced iron (397 mg, 7.10 mmol) was added, and the mixture was stirred at 100° C. overnight. Since the starting material did not disappear, reduced iron (397 mg, 7.10 mmol) was added, and the mixture was further stirred at 100° C. overnight. The mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. To the obtained residue was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and purified by silica gel column chromatography (chloroform/methanol=9/1 v/v) to give 3-(difluoromethoxy)pyridin-2-amine (250 mg, 66%).