[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[CH3:14])(=[O:4])=[O:3].O.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)C>[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([CH:8]=[CH:7][C:6]=1[CH3:14])[NH2:11])(=[O:3])=[O:4]2-Methylsulfonyl-1-methyl-4-nitrobenzene (500 mg, 2.3 mmol) was dissolved in absolute ethanol (15 mL). Stannous chloride (2.6 g, 11.6 mmol) was added and the reaction mixture was stirred at 75° C. for 4 hours. The mixture was poured into water (50 mL), pH was adjusted with a saturated solution of sodium carbonate to basic reaction, followed by addition of ethyl acetate (150 mL). The organic phase was extracted with water (2×50 mL), dried (MgSO4) and concentrated in vacuo to give 0.36 g of 3-methylsulfonyl-4-methylaniline as an oil.
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