[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[C:3]=1[CH2:19][CH:20]=[CH2:21].Cl(O)(=O)(=O)=O.[I:27]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>O.O1CCCC1>[I:27][CH2:21][CH:20]1[O:18][C:4]2[N:5]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:6]3[C:11]([C:2](=[O:1])[C:3]=2[CH2:19]1)=[CH:10][CH:9]=[CH:8][N:7]=3
To a solution of 4.0 g. (0.014 moles) of 4-hydroxy-1-phenyl-3-(2-propenyl)-1,8-naphthyridin-2(1H)-one in 380 ml. of tetrahydrofuran, there is added, dropwise, with stirring at 3°-5° C., 4.0 g. of 70% perchloric acid in 11.5 ml. of water, followed by the slow addition of 10.2 g. of N-iodo-succinimide over a period of 45 minutes. The reaction is stirred at room temperature for three hours, treated with a saturated solution of sodium sulfite, and extracted with 2×250 ml. of ether. The organic layer is dried over magnesium sulfate, filtered and concentrated to a solid residue. The crude products are separated on a 60G silica gel column with methanol:chloroform (5:95). The desired fraction is recrystallized from ethyl acetate to yield the title compound, m.p. 178°-180° C.
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