[CH3:1]OS(OC)(=O)=O.[CH3:8][S:9]([C:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][N:12]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+]>[OH-].[Na+]>[CH3:1][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:21])[C:11]([S:9]([CH3:8])=[O:10])=[N:12]1Dimethylsulfate [12.5 g (0.1 mole)] was added gradually to a vigorously stirred solution of 6.5 g (0.0298 mole) of 3-(methylsulfinyl)-4(1H)-cinnolinone in 120 ml of 1N sodium hydroxide solution at 30°C. The temperature rose to 40° as the suspended dimethyl sulfate gradually went into solution over a period of 15 minutes. After an additional one-half hour of stirring, potassium carbonate excess was added to salt-out an oil. The product was extracted into 800 ml of methylene chloride, the solution was dried over K2CO3, charcoaled, filtered and concentrated. Wt 6.4 g (96.7%) mp. 187°-189°C. Recrystallization from 2-propanol-petroleum ether gave pure material, mp. 189°-191°C.
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