Sodium Fluoride → 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester

HRID 280102Notes

Reaction equation

HRID 280102 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]1

Participants

4

Reactant 2

HCID 5235Sodium FluorideHCID 178471877HCID 178471877, compound

Product 1

HCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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-cyclopropylaminoacrylate in 400 ml of anhydrous dimethylformamide. The reaction mixture is then stirred under reflux for 2 hours and, while hot, poured onto ice. The precipitate is filtered off with suction, thoroughly washed with water and dried over calcium chloride at 100° C. in vacuo. 91.2 g of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate of melting point 167°-168° C. are obtained.

Workup

  1. temperatureunder reflux for 2 hours
  2. additionwhile hot, poured onto ice
  3. filtrationThe precipitate is filtered off with suction
  4. washthoroughly washed with water
  5. dry with materialdried over calcium chloride at 100° C. in vacuo

Sources & evidence

ORD record
ord-cffe62231e314e2db4be994c382c6749
Source dataset
uspto-grants-1986_05
Patent number
US04588726

Reaction notes

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