Acetic Acid → 5,6,7,8-Tetrafluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 981127

Reaction equation

HRID 981127 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:28])[C:5]([C:23]([O:25]CC)=[O:24])=[CH:6][N:7]2[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22].S(=O)(=O)(O)O.C(O)(=O)C>O>[F:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:28])[C:5]([C:23]([OH:25])=[O:24])=[CH:6][N:7]2[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 15070037Ethyl 5,6,7,8-tetrafluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 150700385,6,7,8-Tetrafluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

40.1 g of ethyl 5,6,7,8-tetrafluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate are added to a mixture of 28.5 ml of concentrated sulphuric acid, 250 ml of glacial acetic acid and 200 ml of water and the mixture is heated under reflux for 2 hours. The hot solution is poured onto ice and the precipitate is filtered off with suction, washed with water and dried. 34.5 g of the title compound of melting point 250°-252° C. are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. additionThe hot solution is poured onto ice
  4. filtrationthe precipitate is filtered off with suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-c885914f5d934040a2c86a0595f3bafc
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Linked notes

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