Potassium Phosphate, Tribasic → ethyl 6,7,8-trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1353107Notes

Reaction equation

HRID 1353107 reaction equation
[F:1][CH2:2][CH2:3][NH:4][CH:5]=[C:6]([C:12](=[O:23])[C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([F:21])[C:14]=1F)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(C(C)=O)C>[F:21][C:15]1[CH:14]=[C:13]2[C:18](=[C:17]([F:19])[C:16]=1[F:20])[N:4]([CH2:3][CH2:2][F:1])[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]2=[O:23]

Participants

4

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 178472020HCID 178472020, compound

Product 1

HCID 5088135ethyl 6,7,8-trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 96.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1.0 g of ethyl 3-(2-fluoroethylamino)-2-(2,3,4,5-tetrafluorobenzoyl)acrylate was dissolved in 8 ml of methyl ethyl ketone under heating to 75˜80° C. 1.14 g (1.8 eq.) of K3PO4 was added in portions to the reaction mixture, which was then stirred at the same temperature for 1.5 hours. The reaction mixture was filtered under a reduced pressure and washed with 40 ml of dichloromethane. The filtrate was concentrated under a reduced pressure. The resulting residue was dissolved in 20 ml of dichloromethane and then washed with water. The organic layer was concentrated under a reduced pressure to give 0.91 g of ethyl 6,7,8-trifluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate (Yield: 96.8%).

Workup

  1. temperatureunder heating to 75˜80° C
  2. filtrationThe reaction mixture was filtered under a reduced pressure
  3. washwashed with 40 ml of dichloromethane
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. dissolutionThe resulting residue was dissolved in 20 ml of dichloromethane
  6. washwashed with water
  7. concentrationThe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-1692d586bccd43f4b2c084e89794ecb5
Source dataset
uspto-grants-2007_05
Patent number
US07220861B2

Reaction notes

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