S(S([O-])=O)([O-])=O.[Na+].[Na+].[I:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-])=O)=[CH:12][CH:11]=1.N>O.C(O)C>[I:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH2:23])=[CH:12][CH:11]=1A solution of sodium dithionite (85%, 19.7 g, 96 mmol) in water (100 ml) was added to a suspension of N-(4-iodophenyl)-2-nitroaniline (8 g, 24 mmol) in ethanol (400 ml). The resulting mixture was heated under reflux for 45 min, cooled, treated with dilute aqueous ammonia (300 ml) and concentrated under reduced pressure. The resulting white slurry was treated with dilute aqueous ammonia (200 ml), filtered, the collected solid washed with water (100 ml) and dried to give N-(4-iodophenyl)-2-aminoaniline (3.1 g, 43%) as a white solid.
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