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

HRID 36716Notes

Reaction equation

HRID 36716 reaction equation
[Cl:1][C:2]1[C:11]([F:12])=[C:10]([Cl:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:27])[C:5]([C:22]([O:24]CC)=[O:23])=[CH:6][N:7]2[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21].C(O)(=O)C.S(=O)(=O)(O)O>O>[Cl:1][C:2]1[C:11]([F:12])=[C:10]([Cl:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:27])[C:5]([C:22]([OH:24])=[O:23])=[CH:6][N:7]2[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 15070041Ethyl 5,7-dichloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 150700425,7-Dichloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

41.6 g of ethyl 5,7-dichloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate are heated under reflux with 250 ml of acetic acid, 200 ml of water and 28.5 ml of concentrated sulphuric acid for 3 hours. After cooling, the mixture is poured into 2 liter of ice-water and the precipitate is filtered off with suction, washed with water and dried. 35.5 g of 5,7-dichloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are obtained, melting point: 244°-246° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-79c8b6623f194c89ac1fcdab07209b32
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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