Water → 6,7-Difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester

HRID 2371578Notes

Reaction equation

HRID 2371578 reaction equation
Cl[C:2]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:3]=1[C:4]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[C:2]3[C:3](=[CH:21][C:22]([F:26])=[C:23]([F:25])[CH:24]=3)[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 178471928HCID 178471928, compound

Product 1

HCID 104728546,7-Difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19.2 g of ethyl 2-(2-chloro-4,5-difluorobenzoyl)-3-(4-fluoroanilino)-acrylate was dissolved in 95 ml of dimethylformamide, and 8.3 g of potassium carbonate was added thereto. The mixture was heated for 60 minutes at a temperature of from 100° to 110° C. The reaction mixture was returned to room temperature and poured into water. Precipitated crystals were collected by filtration and washed with ethonol. 15.6 g (90%).

Workup

  1. temperatureThe mixture was heated for 60 minutes at a temperature of from 100° to 110° C
  2. customwas returned to room temperature
  3. customPrecipitated crystals
  4. filtrationwere collected by filtration
  5. washwashed with ethonol

Sources & evidence

ORD record
ord-d5dfa755056840968814d914ce0f014e
Source dataset
uspto-grants-1992_03
Patent number
US05093515

Reaction notes

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