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

HRID 610261Notes

Reaction equation

HRID 610261 reaction equation
Cl.C(O)(=O)C.[Br:6][C:7]1[C:8]([F:36])=[C:9]([F:35])[CH:10]=[C:11]2[C:16]=1[N:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([NH:24]C(C)(C)C)[N:18]=1)[CH:14]=[C:13]([C:29]([O:31]CC)=[O:30])[C:12]2=[O:34]>O>[NH2:24][C:19]1[N:18]=[C:17]([N:15]2[C:16]3[C:11](=[CH:10][C:9]([F:35])=[C:8]([F:36])[C:7]=3[Br:6])[C:12](=[O:34])[C:13]([C:29]([OH:31])=[O:30])=[CH:14]2)[CH:22]=[CH:21][C:20]=1[F:23]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 22121280Ethyl 8-bromo-1-[6-(t-butylamino)-5-fluoropyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221212461-(6-Amino-5-fluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4 ml of the mixed solution (1:1) of 4N hydrochloric acid and acetic acid was added 480 mg of ethyl 8-bromo-1-[6-(t-butylamino)-5-fluoropyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, and the mixture was heated under reflux with stirring for 2 hours. After adding 4 ml of distilled water, the solution was allowed to cool, and the precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 345 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-fd220d30c8c640c0ae30f8bd5455212f
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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