[CH3:1][O:2][C:3]1[C:4]([C:9]2[CH:10]=[C:11]([N+:15]([O-])=O)[CH:12]=[CH:13][CH:14]=2)=[N:5][CH:6]=[CH:7][CH:8]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:4]([C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=2)[NH2:15])=[N:5][CH:6]=[CH:7][CH:8]=1A suspension of 3-(3-methoxypyridin-2-yl)nitrobenzene (0.391 g) in ethanol (8 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 120 mg) under a hydrogen atmosphere for 3 hours. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure to give 3-(3-methoxypyridin-2-yl)aniline (0.34 g).
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