5-Morpholino-2-nitroaniline → 4-(Morpholin-4-yl)benzene-1,2-diamine

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([N+:14]([O-])=O)=[C:11]([CH:13]=2)[NH2:12])[CH2:3][CH2:2]1.[H][H]>C(O)C.[Pd]>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:13]=[C:11]([NH2:12])[C:10]([NH2:14])=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

Procedure

5-Morpholino-2-nitroaniline (200 mg, 0.896 mmol) was added to the 10% Pd/C (25 mg) in ethanol (25 mL) and then hydrogen gas (60 psi) was applied for overnight at room temperature. The reaction mixture was filtered through Celite, and the solvent was removed in vacuum. Purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound (150 mg). 1H NMR: (400 MHz, DMSO-d6): δ 6.38 (d, 1H, J=8.0 Hz), 6.18 (d, 1H, J=2.4 Hz), 5.99 (dd, 1H, J=2.4 and 8.4 Hz), 4.35 (bs, 2H), 3.97 (bs, 2H), 3.66 (m, 4H), 2.81 (m, 4H).