C([O:3][C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=2)=[CH:9][C:8]=1[N+:21]([O-])=O)C.C(=O)([O-])O.[Na+]>C(O)(=O)C.[Fe]>[CH3:20][O:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([C:10]2[CH:9]=[C:8]3[C:7]([CH:6]=[CH:5][C:4](=[O:3])[NH:21]3)=[CH:12][CH:11]=2)[CH:18]=1To a suspension of 4-(4-methoxypyridin-2-yl)-2-nitrocinnamic acid ethyl ester (659 mg) in acetic acid (11 ml) was added iron powder (673 mg), and the mixture was stirred at 100° C. for 2 hours. After cooling, the reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution and filtered, and the filtrate was extracted with dichloromethane-methanol (5:1). The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was dissolved in ethanol (5 ml). To the solution was added a solution of sodium methoxide in methanol (28%, 3 ml), and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give 7-(4-methoxypyridin-2-yl)-2-quinolone (140 mg).
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