2-Methyl-5-nitrobenzene-1-sulfonamide → 5-Amino-2-[(E)-2-(4-amino-2-(aminosulfonyl)phenyl)ethenyl]benzenesulfonamide

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In a round bottom flask under nitrogen was placed 5-nNitro-2-[(E)-2-(4-nitro-2-(aminosulfonyl)phenyl)ethenyl]benzenesulfonamide (Example 51, 0.38 g, 0.887 mmol) and 40 mL of ethyl acetate added. To this mixture was added tin chloride dihydrate (1.00 g, 4.44 mmol) and a reflux condenser was attached. The solution was heated in an oil bath to 80 C. and stirred for 16 hours. After cooling to room temperature the solution was diluted with ethyl acetate (250 mL) and washed with saturated sodium bicarbonate. The whole mixture was filtered thru Celite and the aqueous layer discarded. The organics were then washed with brine, dried (MgSO4) and concentrated on a rotovap to dryness. The crude material was then recrystallized from 10% methanol/dichloromethane and dried under vacuum to afford 100 mg of the title compound as a dark yellow solid (31%): 1HNMR (DMSO-d6) δ7.58 (d, J=8.5 Hz, 2H), 7.49 (s, 2H), 7.31 (br s, 4H), 7.15 (d, J=2 Hz, 2H), 6.75 (dd, J=8.5 Hz, 2 Hz, 2H), 5.65 (br s, 4H).

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