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

HRID 1274680Notes

Reaction equation

HRID 1274680 reaction equation
Cl.C(O)(=O)C.[Cl:6][C:7]1[C:8]([F:43])=[C:9]([F:42])[CH:10]=[C:11]2[C:16]=1[N:15]([C:17]1[C:22]([F:23])=[C:21]([CH3:24])[C:20]([F:25])=[C:19]([NH:26]CC3C=CC(OC)=CC=3)[N:18]=1)[CH:14]=[C:13]([C:36]([O:38]CC)=[O:37])[C:12]2=[O:41]>O>[NH2:26][C:19]1[N:18]=[C:17]([N:15]2[C:16]3[C:11](=[CH:10][C:9]([F:42])=[C:8]([F:43])[C:7]=3[Cl:6])[C:12](=[O:41])[C:13]([C:36]([OH:38])=[O:37])=[CH:14]2)[C:22]([F:23])=[C:21]([CH3:24])[C:20]=1[F:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 22121289Ethyl 8-chloro-1-[3,5-difluoro-6-(p-methoxybenzylamino)-4-methylpyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221211871-(6-Amino-3,5-difluoro-4-methylpyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of 2.5 ml of 4N hydrochloric acid and 2.5 ml of acetic acid was added all amount of the above described ethyl 8-chloro-1-[3,5-difluoro-6-(p-methoxybenzylamino)-4-methylpyridine-2-yl]-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 and stand. To the residue was added 10 ml of distilled water, and the solution was concentrated under reduced pressure. The procedure of adding 10 ml of ethanol and concentrating the solution under reduced pressure was repeated three times, and 6 ml of chloroform was added to the residue, and the mixture was heated under reflux with stirring for 1 hour and allowed to cool. The precipitate was collected by filtration, and washed with ethanol and diisopropylether successively to obtain 128 mg of the title compound as a colorless powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureto cool
  4. concentrationthe solution was concentrated under reduced pressure
  5. additionThe procedure of adding 10 ml of ethanol
  6. concentrationconcentrating the solution under reduced pressure
  7. additionwas added to the residue
  8. temperaturethe mixture was heated
  9. temperatureunder reflux
  10. stirringwith stirring for 1 hour
  11. temperatureto cool
  12. filtrationThe precipitate was collected by filtration
  13. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-f8bc3372c1d14eb3a9fe7400a69f058c
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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