[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([N+:13]([O-])=O)[CH:8]=[C:9]([CH3:12])[C:10]=1[F:11])(=[O:4])=[O:3].C(O)C.[Cl-].[NH4+]>[Fe].O>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([CH3:12])[C:10]=1[F:11])[NH2:13])(=[O:4])=[O:3]To a heterogeneous solution of 3-aminosulfonyl-4-fluoro-5-methylnitrobenzene (27) (0.5 g, 2 mmol) in of ethanol:water (50 mL, each) were added iron powder (1.08 g, 20 mmol), and ammonium chloride (1.08 g, 20 mmol) at room temperature. The resulting heterogeneous mixture was then stirred at 60° C. for 2 hours, filtered through celite (when hot), washed with ethanol (2×50 mL) and then the solvent was removed under reduced pressure. The residue upon dilution with water was extracted with ethyl acetate (3×50 mL), and the organic phase was dried over anhydrous sodium sulfate and concentrated under a reduced pressure to obtain 3-aminosulfonyl-4-fluoro-5-methylaniline (28). LCMS: purity: 85%; MS (m/z): 205 (MH+).
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