[N+:1]([C:4]1[C:9]2[S:10](=[O:14])(=[O:13])[CH:11]=[CH:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[C:9]2[S:10](=[O:14])(=[O:13])[CH2:11][CH2:12][C:8]=2[CH:7]=[CH:6][CH:5]=17-Nitrobenzo[b]thiophene-1,1-dioxide (19 g, Example 17) was hydrogenated in 200 ml of ethyl acetate over 1.0 g of 10% palladium-on-charcoal catalyst at 500 pounds-per-square-inch of pressure and 100° C. until no more hydrogen gas was absorbed. The mixture was filtered through celite, and the filtrate was concentrated in vacuo. The solid residue was recrystallized from 1-chlorobutane to yield 13.2 g of the title compound; m.p. 117°-119° C.
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