[CH2:1]([NH:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[NH2:10][C:9]1[C:4]([NH:3][CH2:1][CH3:2])=[N:5][CH:6]=[CH:7][CH:8]=1A solution of 2-(ethylamino)-3-nitropyridine (52 g) in MeOH (600 mL) was stirred overnight at room temperature under hydrogen (1 atm.) in the presence of 20% Pd(OH)2/C (10.4 g). The catalyst was removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure to give the title compound as a black solid (39 g, 88% yield over steps a) and b).
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