Acetic Acid → 8-Chloro-6,7-difluoro-1-(3,5-difluoro-6-ethylaminopyridin-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1274675Notes

Reaction equation

HRID 1274675 reaction equation
Cl.[C:2](O)(=O)[CH3:3].[Cl:6][C:7]1[C:8]([F:34])=[C:9]([F:33])[CH:10]=[C:11]2[C:16]=1[N:15]([C:17]1[C:22]([F:23])=[CH:21][C:20]([F:24])=[C:19]([NH:25]C)[N:18]=1)[CH:14]=[C:13]([C:27]([O:29]CC)=[O:28])[C:12]2=[O:32]>O>[Cl:6][C:7]1[C:8]([F:34])=[C:9]([F:33])[CH:10]=[C:11]2[C:16]=1[N:15]([C:17]1[C:22]([F:23])=[CH:21][C:20]([F:24])=[C:19]([NH:25][CH2:2][CH3:3])[N:18]=1)[CH:14]=[C:13]([C:27]([OH:29])=[O:28])[C:12]2=[O:32]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 15896297Ethyl 8-chloro-6,7-difluoro-1-(3,5-difluoro-6-methylamino-pyridin-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221211818-Chloro-6,7-difluoro-1-(3,5-difluoro-6-ethylaminopyridin-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3 ml of a mixed solution (1:1, v/v) of 4 ml of 4N hydrochloric acid and 1 ml of acetic acid was added 510 mg of ethyl 8-chloro-6,7-difluoro-1-(3,5-difluoro-6-methylamino-pyridin-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate, and the mixture was heated under reflux with stirring for 2.5 hours. After adding 2 ml of distilled water, the mixture was allowed to cool, and the precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 454 mg of the title compound as a gray powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureto cool
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-462d1218d84e40a4ba5f2bb800743889
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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