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 1274773Notes

Reaction equation

HRID 1274773 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-difluoropyridine-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-6d8fc322a2eb41fe933ac5df761abe2d
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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