5-Nitro-2-(2,2,2-trifluoroethoxy)pyridine → 6-(2,2,2-Trifluoroethoxy)pyridin-3-amine

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[N:8][CH:9]=1)([O-])=O.[H][H]>CO.[Pd]>[F:15][C:12]([F:13])([F:14])[CH2:11][O:10][C:7]1[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

Procedure

5-Nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine (20.5 g, obtained in example 108, step 1) was dissolved in methanol (160 mL). Palladium on activated charcoal (1.96 g, 10% Pd) was added and an atmosphere of hydrogen was introduced at RT. The mixture was stirred under hydrogen for 72 hours. The reaction mixture was filtered over dicalite speed plus (Acros Organics), washed with ethyl acetate and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a brown liquid (16.49 g, 91%). MS (m/e): 193.1 [MH+].