N[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].N([O-])=[O:19].[Na+].O>Cl.CO>[OH:19][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]To a mixture of methyl 3-amino-5-[methyl(methylsulfonyl)amino]benzoate 1.29 g (5.0 mmol) in 2N hydrochloric acid (10 mL) and methanol (15 mL) was added sodium nitrite 0.759 g (11 mmol) under ice-cooling. Thereto was further added water (20 mL) and the mixture was stirred at 70° C. for 2 hours. The mixture was extracted twice with ethyl acetate (30 mL) and dried on magnesium sulfate and the solvent was evaporated to give 1.33 g (5.0 mmol) of the title compound (yield: 100%).
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