Hydrochloric Acid → 5-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 610281Notes

Reaction equation

HRID 610281 reaction equation
Cl.[NH2:2][C:3]1[C:12]([F:13])=[C:11]([F:14])[C:10]([F:15])=[C:9]2[C:4]=1[C:5](=[O:30])[C:6]([C:25]([O:27]CC)=[O:26])=[CH:7][N:8]2[C:16]1[C:21]([F:22])=[CH:20][C:19]([F:23])=[C:18]([NH2:24])[N:17]=1>C(O)(=O)C>[NH2:2][C:3]1[C:12]([F:13])=[C:11]([F:14])[C:10]([F:15])=[C:9]2[C:4]=1[C:5](=[O:30])[C:6]([C:25]([OH:27])=[O:26])=[CH:7][N:8]2[C:16]1[C:21]([F:22])=[CH:20][C:19]([F:23])=[C:18]([NH2:24])[N:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22121240Ethyl 5-amino-1-(6-amino-3,5-difluoropyridin-2-yl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221212615-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 95.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 1.5 ml of the mixed solution (1:1) of 4N hydrochloric acid and acetic acid was added 145 mg of ethyl 5-amino-1-(6-amino-3,5-difluoropyridin-2-yl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, and the mixture was heated under reflux for 17 hours with stirring and allowed to cool. The precipitate was collected by filtration, and washed with ethanol and to obtain 129 mg of the title compound as a yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 17 hours
  3. temperatureto cool
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-51cc96561d5f4a948698154d0e4ee335
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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