[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH:11]([CH2:16][N+:17]([O-])=O)[CH2:12][N+:13]([O-])=O>[Pt].[Pd].[Ni].CO>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH:11]([CH2:16][NH2:17])[CH2:12][NH2:13])=[C:2]([CH3:1])[CH:7]=1A pressure flask was charged with 2-methyl-4-nitro-1-(2-nitro-1-nitromethyl-ethyl)-benzene (29.6 g, 0.11 mol), 10 wt % platinum on carbon (3.0 g), 10 wt % palladium on carbon (9.0 g, 50 wt % water), Raney nickel (9.0 g, wet), and methanol (740 mL) under a nitrogen blanket. After attaching the flask to the hydrogenation apparatus, it was subjected to three vacuum degas-nitrogen purge cycles, followed by three nitrogen outgas-hydrogen purge cycles. The vigorously stirred suspension was held under 60 psi hydrogen pressure at 55-60° C. for at least 72 h. The reaction mixture was filtered through a celite pad (15 g) rinsing with methanol (600 mL). The filtrate was concentrated to dryness under reduced pressure to give the crude title compound as a red-brown gum (20 g, 100% yield).
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