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 610195Notes

Reaction equation

HRID 610195 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-trifluoropyridin-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-749b3876fdf54143a31df09e03bece87
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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