[CH3:1][C:2]1[O:3][C:4]2[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=2[C:6](=[O:11])[C:7]=1[N+:8]([O-])=O>[Pd].C(O)C>[CH3:1][C:2]1[O:3][C:4]2[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=2[C:6](=[O:11])[C:7]=1[NH2:8]A mixture of 2-methyl-3-nitro-4H-1-benzopyran-4-one (5.0g, 0.244 mole) and 10% palladium on charcoal (0.75g) in ethanol (250 ml) was shaken under a hydrogen atmosphere in a Parr shaker for 40 minutes. The catalyst was filtered off, and the solvent was removed under reduced pressure to give yellow solids. Recrystallization from benzene gave yellow crystals (2.4g, 56%), m.p. 118°-20° C.
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