[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([N+:8]([O-])=O)[CH:7]=1.[Cl-].[NH4+].C(O)C.[OH-].[Na+]>[Fe].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:7]=1)[NH2:8]A slurry of 5-bromo-2-methylnitrobenzene (3.00 g), iron powder (3.11 g), and ammonium chloride (2.97 g), in 3:1 ethanol : water (50 ml) was heated at reflux temperature for 1 hour. The mixture was poured into 10% aqueous sodium hydroxide and filtered through Celite®. The filtrate was then extracted with ethyl acetate, the extracts washed with brine, dried over magnesium sulfate, filtered and evaporated to afford the subtitle compound as an oil (2.64 g).
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