Diazald → 2(1H)-Quinolinone, 3-methoxy-

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N1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[N+:12](=[CH2:14])=[N-].[CH3:15]C1C=CC(S(N(N=O)C)(=O)=O)=CC=1>CCOCC>[CH3:15][O:5][C:4]1[C:2](=[O:3])[NH:12][C:14]2[C:7]([CH:6]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2

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To a mixture of 1.05 g (7.1 mmol) of isatin in 15 mL of ether in ice-bath was added dropwise a solution of diazomethane in ether (prepared from 4.4 g (20 mmol) of Diazald according to Aldrichimica Acta 16:3 (1983)). The resulting solution was stirred in ice-bath for 3 h then room temperature overnight. The mixture was filtered and dried to leave white solid 0.684 g (52%), mp 188°-189° C. (lit. 191° C.; Greibrokk and Undheim, Acta Chem. Scand. 25:2935 (1971)). 1H NMR (CDCl3) 3.977 (s, 3), 7.014 (s, 1), 7.21 (m, 1), 7.39 (m, 2), 7.509 (d, 1, J=7.8), 11.429 (s, 1).