Sodium Fluoride → 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester
Reaction equation
[F-].[Na+].F[C:4]1[C:22]([F:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:5]=1[C:6]([C:8](=[CH:14][NH:15][CH:16]1[CH2:18][CH2:17]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7]>CN(C)C=O>[CH:16]1([N:15]2[C:19]3[C:5](=[CH:4][C:22]([F:23])=[C:21]([F:24])[C:20]=3[F:25])[C:6](=[O:7])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14]2)[CH2:18][CH2:17]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
21.2 g of sodium fluoride are added to a solution of 107.8 g of ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-cyclopropylamino-acrylate (6) in 400 ml of anhydrous dimethylformamide. Thereafter, the mixture is stirred under reflux for 2 hours, and the hot reaction mixture is poured onto ice. The precipitate is filtered off under suction, washed thoroughly with water and dried over calcium chloride in vacuo at 100° C. 91.2 g of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (7) of melting point 167°-168° C. are obtained.