[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:3]=1[NH2:4]>CO.[Pd]>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[C:3]=1[NH2:4]A solution of 2-chloro-6-nitroaniline (1.0 g, 5.81 mmol, commercially available from Apollo International) in methanol (20 mL) was passed through the H-Cube® (Thales Nanotechnology Inc.) operating at 40 bars and ambient temperature with a flow rate of 1 mL/min. The H-Cube® was equipped with a 10% Pd/C cartridge (Catcart™). The reaction mixture was collected and concentrated after being exposed to the hydrogenation conditions. The crude 3-chlorobenzene-1,2-diamine was carried on without further purification. MS (EI): 145 (MH+).
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