Potassium Phosphate, Tribasic → Ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1353100Notes

Reaction equation

HRID 1353100 reaction equation
Cl[C:2]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:3]=1[C:4]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[N:13]1[C:2]2[C:3](=[CH:22][C:23]([F:27])=[C:24]([F:26])[CH:25]=2)[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12]1

Participants

4

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 178471931HCID 178471931, compound

Product 1

HCID 10474002Ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8.0 g of ethyl 2-(2-chloro-4,5-difluorobenzoyl)-3-(2,4-difluorophenylamino)acrylate was dissolved in 80 ml of acetonitrile under heating to 75˜80° C. 11.84 g (2.8 eq.) of K3PO4 was added in portions to the reaction mixture, which was then stirred at the same temperature for 2 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 88 ml of dichloromethane and then washed with water. The organic layer was concentrated under a reduced pressure to give 6.69 g of ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (Yield: 92%).

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 88 ml of dichloromethane
  6. washwashed with water
  7. concentrationThe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-f9312b4874d64177ba5ab76cfa2720cd
Source dataset
uspto-grants-2007_05
Patent number
US07220861B2

Reaction notes

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