[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[CH2:4][CH2:3]1>CO.[Pd]>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][N:2]2[CH3:1])=[CH:6][CH:7]=11-Methyl-6-nitroindoline (0.9 g) was hydrogenated at 40 psi in methanol (100 ml) containing 10% palladium on carbon (0.9 g). The reaction mixture was filtered then evaporated and the residue was purified by column chromatography on silica using hexane→50% ethyl acetate/hexane to afford the title compound (0.62 g).
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