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

HRID 368470Notes

Reaction equation

HRID 368470 reaction equation
Cl.C(O)(=O)C.[NH2:6][C:7]1[N:12]=[C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([F:25])=[C:20]([F:24])[C:21]=3[Cl:23])[C:16](=[O:26])[C:15]([C:27]([O:29]CC)=[O:28])=[CH:14]2)[C:10]([CH3:32])=[CH:9][C:8]=1[F:33]>O>[NH2:6][C:7]1[N:12]=[C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([F:25])=[C:20]([F:24])[C:21]=3[Cl:23])[C:16](=[O:26])[C:15]([C:27]([OH:29])=[O:28])=[CH:14]2)[C:10]([CH3:32])=[CH:9][C:8]=1[F:33]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 22121228Ethyl 1-(6-amino-5-fluoro-3-methylpyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221212361-(6-Amino-5-fluoro-3-methylpyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 800 mg of the mixed solution (1:1) of 4N hydrochloric acid and acetic acid was added 160 mg of ethyl 1-(6-amino-5-fluoro-3-methylpyridine-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, and the mixture was heated under reflux with stirring for 30 minutes. After adding 0.5 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 145 mg of the title compound as a pale brown 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-ee82a600b38642fa98c1f4bede7e0c75
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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