Hydrochloric Acid → 1-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 610173Notes

Reaction equation

HRID 610173 reaction equation
Cl.[Cl:2][C:3]1[C:4]([F:38])=[C:5]([F:37])[CH:6]=[C:7]2[C:12]=1[N:11]([C:13]1[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([NH:21]CC3C=CC(OC)=CC=3)[N:14]=1)[CH:10]=[C:9]([C:31]([O:33]CC)=[O:32])[C:8]2=[O:36]>C(O)(=O)C>[NH2:21][C:15]1[N:14]=[C:13]([N:11]2[C:12]3[C:7](=[CH:6][C:5]([F:37])=[C:4]([F:38])[C:3]=3[Cl:2])[C:8](=[O:36])[C:9]([C:31]([OH:33])=[O:32])=[CH:10]2)[C:18]([F:19])=[CH:17][C:16]=1[F:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15434902Ethyl 8-chloro-1-[3,5-difluoro-6-(p-methoxybenzylamino)pyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 154349011-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 57.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixed solution of 6 ml of 4N hydrochloric acid and 6 ml of acetic acid was added 3.00 g of ethyl 8-chloro-1-[3,5-difluoro-6-(p-methoxybenzylamino)pyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, and the mixture was heated under reflux with stirring for 16 hours. The solution was allowed to cool and stand, and the precipitate was collected by decantation, and washed by adding a small amount of distilled water, shaking, allowing to stand, and decanting. To the precipitate was added 10 ml of ethanol, and the mixture was heated under reflux with stirring for 1 hour and allowed to cool and stand, and the precipitate was collected by decantation. To this precipitate was again added 10 ml of chloroform, and the mixture was stirred under reflux condition for 1 hour and allowed to cool, and the precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 1.25 g of the title compound as a pale brown powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureto cool
  4. customthe precipitate was collected by decantation
  5. washwashed
  6. additionby adding a small amount of distilled water
  7. stirringshaking
  8. customdecanting
  9. additionTo the precipitate was added 10 ml of ethanol
  10. temperaturethe mixture was heated
  11. temperatureunder reflux
  12. stirringwith stirring for 1 hour
  13. temperatureto cool
  14. customthe precipitate was collected by decantation
  15. stirringthe mixture was stirred
  16. temperatureunder reflux condition for 1 hour
  17. temperatureto cool
  18. filtrationthe precipitate was collected by filtration
  19. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-5fe08d17ab0d4120b46139b7ef8ec1e5
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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