[F:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6][NH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:27](I)[CH3:28]>CN(C)C=O>[CH2:27]([N:7]1[C:8]2[C:3](=[C:2]([F:1])[C:11]([F:12])=[C:10]([F:13])[C:9]=2[F:14])[C:4](=[O:20])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6]1)[CH3:28]To 38.5 g (134 mmol) of 5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester in 700 ml of N,N-dimethylformamide was added 37.15 g (two equivalents) of potassium carbonate and 50 ml (five equivalents) of ethyl iodide. The mixture was brought to 50° C. and stirred vigorously overnight. The solvents were removed and the residue partioned between water and dichloromethane. The dichloromethane was dried (magnesium sulfate) and concentrated. The residue was triturated with diethyl ether to give 30.5 g of material which was recrystallized from ethanol. Filtration gave 23.5 g of the title compound, mp 217°-220° C.
Loading…
