F[C:2]1[C:24]([O:25][CH:26]([F:28])[F:27])=[C:23]([F:29])[C:22]([F:30])=[CH:21][C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C(=O)([O-])O.[Na+].O>CN(C)C=O>[F:30][C:22]1[CH:21]=[C:3]2[C:2](=[C:24]([O:25][CH:26]([F:28])[F:27])[C:23]=1[F:29])[N:13]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4]2=[O:5]In 50 ml of N,N-dimethylformamide was dissolved 5.6 g (0.013 mole) of ethyl 2-(2,4,5-trifluoro-3-difluoromethoxybenzoyl)-3-(2-pyridylmethylamino)acrylate, and 2.2 g (0.026 mole) of sodium hydrogen carbonate was added thereto. The mixture was stirred at 120° C. for 30 minutes. Then, the reaction mixture was poured into 200 ml of water, and crystals precipitated were collected by filtration. The collected crystals were washed with water and ethanol and dried to obtain 2.6 g of ethyl 6,7-difluoro-8-difluoromethoxy-1-(2-pyridylmethyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate as yellow crystals.
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