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

HRID 368434Notes

Reaction equation

HRID 368434 reaction equation
Cl.C(O)(=O)C.[Br:6][C:7]1[C:8]([F:37])=[C:9]([F:36])[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(C)(C)C)[N:18]=1)[CH:14]=[C:13]([C:30]([O:32]CC)=[O:31])[C:12]2=[O:35]>O>[NH2:25][C:19]1[N:18]=[C:17]([N:15]2[C:16]3[C:11](=[CH:10][C:9]([F:36])=[C:8]([F:37])[C:7]=3[Br:6])[C:12](=[O:35])[C:13]([C:30]([OH:32])=[O:31])=[CH:14]2)[C:22]([F:23])=[CH:21][C:20]=1[F:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 15434899Ethyl 8-bromo-1-[6-(t-butylamino)-3,5-difluoro-pyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 154869771-(6-Amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of 3.5 ml of 4N hydrochloric acid and 3.5 ml of acetic acid was added 1.38 g of ethyl 8-bromo-1-[6-(t-butylamino)-3,5-difluoropyridine-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, and the mixture was heated under reflux with stirring for 5 hours. After adding 5 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 1.10 g 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-8c2587328dcd41c6a50bcecada496909
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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