Hydrochloric Acid → 1-(6-Amino-3,5-difluoropyridin-2-yl)-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 368499Notes

Reaction equation

HRID 368499 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7]([N:9]2[C:18]3[C:13](=[C:14]([F:22])[C:15]([F:21])=[C:16]([F:20])[C:17]=3[F:19])[C:12](=[O:23])[C:11]([C:24]([O:26]CC)=[O:25])=[CH:10]2)[C:6]([F:29])=[CH:5][C:4]=1[F:30]>C(O)(=O)C>[NH2:2][C:3]1[N:8]=[C:7]([N:9]2[C:18]3[C:13](=[C:14]([F:22])[C:15]([F:21])=[C:16]([F:20])[C:17]=3[F:19])[C:12](=[O:23])[C:11]([C:24]([OH:26])=[O:25])=[CH:10]2)[C:6]([F:29])=[CH:5][C:4]=1[F:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22121241Ethyl 1-(6-amino-3,5-difluoropyridin-2-yl)-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221212481-(6-Amino-3,5-difluoropyridin-2-yl)-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 93.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 2 ml of the mixed solution (1:1) of 4N hydrochloric acid and acetic acid was added 320 mg of ethyl 1-(6-amino-3,5-difluoropyridine-2-yl)-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, and the mixture was heated under reflux for 3 hours with stirring, and allowed to cool. The precipitate was collected by filtration, and washed with ethanol to obtain 280 mg of the title compound as a colorless powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-79d9c8b321f5477291dacb53e5277a92
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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