[CH:1]1([CH2:4][NH:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=2[N+:14]([O-])=O)[CH2:3][CH2:2]1>C(O)C>[CH:1]1([CH2:4][NH:5][C:6]2[C:7]([NH2:14])=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=2)[CH2:2][CH2:3]1N-(Cyclopropylmethyl)-4-methoxy-2-nitroaniline (8-1, 175 g) was dissolved in ethanol (1750 mL) and was added to a 4.0 L Hast ‘C” Shaker can. The mixture was cooled to 10° C. and treated with 3% Pt/0.6% VG/C, deGussa (4.5 g). The vessel was sparged under nitrogen and then sparged three times with hydrogen at a setting of 40 psi and agitated for 2.5 hours. To a pre-washed solka-flok with ethanol, the reaction mixture was filtered through solka-flok through a sintered glass funnel to have about a ½ inch depth of solka-flok. The solka-flok was then washed with 1 L ethanol and concentrated in vacuo, providing the titled compound 8-2.
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