[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:14]=[CH:15][C:16]=1[NH2:17]To a solution of 3-chloro-N-(2-morpholinoethyl)-4-nitroaniline (3.50 g, 12.25 mmol) in EtOAc (60 mL) was added catalyst Pd/C (0.73 g). The reaction was stirred at rt under H2 overnight, then filtered. The filtrate was concentrated in vacuo to give the crude product for the next step without further purification.
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