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

HRID 1274685Notes

Reaction equation

HRID 1274685 reaction equation
C([NH:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[N:9]=[C:8]([N:14]2[C:23]3[C:18](=[CH:19][C:20]([F:26])=[C:21]([F:25])[C:22]=3[Cl:24])[C:17](=[O:27])[C:16]([C:28]([O:30]CC)=[O:29])=[CH:15]2)[C:7]=1[F:33])(C)(C)C.Cl>C(O)(=O)C>[NH2:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[N:9]=[C:8]([N:14]2[C:23]3[C:18](=[CH:19][C:20]([F:26])=[C:21]([F:25])[C:22]=3[Cl:24])[C:17](=[O:27])[C:16]([C:28]([OH:30])=[O:29])=[CH:15]2)[C:7]=1[F:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22121213Ethyl 1-(4-t-butylamino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221212331-(4-Amino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 67.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 300 mg of ethyl 1-(4-t-butylamino-3,5,6-trifluoropyridine-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate were added 3 ml of 12N hydrochloric acid and 0.5 ml of acetic acid, and the mixture was heated under reflux for 1.5 hour. The reaction solution was allowed to cool, and the solid precipitated was collected by filtration and washed with ethanol and diethylether successively to obtain 168 mg of the title compound as a colorless powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hour
  3. temperatureto cool
  4. customthe solid precipitated
  5. filtrationwas collected by filtration
  6. washwashed with ethanol and diethylether successively

Sources & evidence

ORD record
ord-9b9d13836d134fcc984df5f4cc011a7f
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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