Ethyl 1-(3-tert-butoxycarbonylamino-4,6-difluorophenyl)-6,7-difluoro-5,8-dimethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate → 1-(3-amino-4,6-difluorophenyl)-6,7-difluoro-5,8-dimethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 322820Notes

Reaction equation

HRID 322820 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([N:17]2[C:26]3[C:21](=[C:22]([CH3:30])[C:23]([F:29])=[C:24]([F:28])[C:25]=3[CH3:27])[C:20](=[O:31])[C:19]([C:32]([O:34]CC)=[O:33])=[CH:18]2)[C:12]([F:16])=[CH:13][C:14]=1[F:15])=O)(C)(C)C>Cl>[NH2:8][C:9]1[CH:10]=[C:11]([N:17]2[C:26]3[C:21](=[C:22]([CH3:30])[C:23]([F:29])=[C:24]([F:28])[C:25]=3[CH3:27])[C:20](=[O:31])[C:19]([C:32]([OH:34])=[O:33])=[CH:18]2)[C:12]([F:16])=[CH:13][C:14]=1[F:15]

Participants

3

Reactant 1

HCID 22011365Ethyl 1-(3-tert-butoxycarbonylamino-4,6-difluorophenyl)-6,7-difluoro-5,8-dimethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 155184811-(3-amino-4,6-difluorophenyl)-6,7-difluoro-5,8-dimethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidYield 89.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 1.8 g of the ethyl 1-(3-tert-butoxycarbonylamino-4,6-difluorophenyl)-6,7-difluoro-5,8-dimethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate obtained in the Reference Example 15 was added 10 ml of 12N hydrochloric acid, and the mixture was stirred under heating and reflux condition for 4 hours. After allowing to cool, the solid precipitate was collected by filtration, washed with water and ethanol successively, and dried to obtain 1.2 g of the title compound.

Workup

  1. temperatureunder heating
  2. temperaturereflux condition for 4 hours
  3. temperatureto cool
  4. filtrationthe solid precipitate was collected by filtration
  5. washwashed with water and ethanol successively
  6. customdried

Sources & evidence

ORD record
ord-be8b403130484382b314e6683ebfb9be
Source dataset
uspto-grants-2001_04
Patent number
US06211375B1

Reaction notes

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