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 368421Notes

Reaction equation

HRID 368421 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-37a62a2f6a124a1c99276e4901b36a9c
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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