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

HRID 368452Notes

Reaction equation

HRID 368452 reaction equation
Cl.C(O)(=O)C.C([NH:10][C:11]1[N:16]=[C:15]([N:17]2[C:26]3[C:21](=[CH:22][C:23]([F:29])=[C:24]([F:28])[C:25]=3[Cl:27])[C:20](=[O:30])[C:19]([C:31]([O:33]CC)=[O:32])=[CH:18]2)[CH:14]=[CH:13][C:12]=1[F:36])(C)(C)C>O>[NH2:10][C:11]1[N:16]=[C:15]([N:17]2[C:26]3[C:21](=[CH:22][C:23]([F:29])=[C:24]([F:28])[C:25]=3[Cl:27])[C:20](=[O:30])[C:19]([C:31]([OH:33])=[O:32])=[CH:18]2)[CH:14]=[CH:13][C:12]=1[F:36]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 22121243Ethyl 1-[6-(t-butylamino)-5-fluoropyridin-2-yl]-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221212661-(6-Amino-5-fluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2 ml of mixed solution (1:1) of 4N hydrochloric acid and acetic acid was added 450 mg of ethyl 1-[6-(t-butyl-amino)-5-fluoropyridine-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. After adding 1 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 342 mg of the title compound as a colorless 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-d25056a78783443886e73fa609b0b387
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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