[CH2:1]([O:3][C:4](=[O:22])[CH:5]=[CH:6][CH:7]=[CH:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=1[N+:19]([O-])=O)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=1[NH2:19])[CH3:2]To a solution of 5-(4,5-dimethoxy-2-nitro-phenyl)-penta-2,4-dienoic acid ethyl ester (Step A, 0.5 g, 1.63 mmol) in EtOH (15 mL) at RT was added Pd/C (0.05 g). The flask was capped with a rubber septum and H2 pressure was applied through a balloon/needle. The reaction was stirred at RT for 12 h, at which time the mixture was filtered through sand/Celite®. The solvent was removed under reduced pressure to afford the title compound.
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