Hydrochloric Acid → 7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 248504

Reaction equation

HRID 248504 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:19]([O:21]CC)=[O:20])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[F:25].[OH-].[Na+].O.Cl>C(O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:19]([OH:21])=[O:20])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[F:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 136069047-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester

Product 1

HCID 573387-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 320 mg of the above ester, 5 ml of 1N sodium hydroxide, 5 ml of water and 5 ml of ethanol was heated for 30 minutes, then cooled and adjusted to pH 7 with dilute hydrochloric acid. The solid was collected, giving 280 mg of 7-chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.

Workup

  1. temperaturewas heated for 30 minutes
  2. temperaturecooled
  3. customThe solid was collected

Sources & evidence

ORD record
ord-065be0e4b2e0425283474b50a6c3738b
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Linked notes

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