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

HRID 610239Notes

Reaction equation

HRID 610239 reaction equation
Cl.[NH2:2][C:3]1[C:8]([F:9])=[CH:7][N:6]=[C:5]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:22])=[C:17]([F:21])[C:18]=3[Cl:20])[C:13](=[O:23])[C:12]([C:24]([O:26]CC)=[O:25])=[CH:11]2)[CH:4]=1>C(O)(=O)C>[NH2:2][C:3]1[C:8]([F:9])=[CH:7][N:6]=[C:5]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:22])=[C:17]([F:21])[C:18]=3[Cl:20])[C:13](=[O:23])[C:12]([C:24]([OH:26])=[O:25])=[CH:11]2)[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22121193Ethyl 1-(4-amino-5-fluoropyridine-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221211881-(4-Amino-5-fluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 400 mg of the mixed solution (1:1) of 4N hydrochloric acid and acetic acid was added 35 mg of ethyl 1-(4-amino-5-fluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, and the mixture was heated under reflux with stirring for 3 hours and allowed to cool. The precipitate was collected by filtration, and washed with distilled water, ethanol and diisopropylether successively to obtain 31 mg of the title compound as a pale yellow powder.

Workup

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

Sources & evidence

ORD record
ord-72a48e2ab03940d8ac50d2dcfacc2eef
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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