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

HRID 610273Notes

Reaction equation

HRID 610273 reaction equation
Cl.[Cl:2][C:3]1[C:4]([F:32])=[C:5]([F:31])[CH:6]=[C:7]2[C:12]=1[N:11]([C:13]1[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([NH:21][CH:22]([CH3:24])[CH3:23])[N:14]=1)[CH:10]=[C:9]([C:25]([O:27]CC)=[O:26])[C:8]2=[O:30]>C(O)(=O)C>[Cl:2][C:3]1[C:4]([F:32])=[C:5]([F:31])[CH:6]=[C:7]2[C:12]=1[N:11]([C:13]1[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([NH:21][CH:22]([CH3:24])[CH3:23])[N:14]=1)[CH:10]=[C:9]([C:25]([OH:27])=[O:26])[C:8]2=[O:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22121250Ethyl 8-chloro-6,7-difluoro-1-(3,5-difluoro-6-isopropylamino-pyridine-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221212218-Chloro-6,7-difluoro-1-(3,5-difluoro-6-isopropylaminopyridin-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 94.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 3 ml of the mixed solution of 4N hydrochloric acid and acetic acid (1:1, v/v) was added 300 mg of ethyl 8-chloro-6,7-difluoro-1-(3,5-difluoro-6-isopropylaminopyridin-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate, and the mixture was heated under reflux for 19 hours with stirring. The precipitate was collected by filtration, washed with ethanol and diisopropylether successively to obtain 265 mg of the title compound as a yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 19 hours
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-16278972d15c4b83af2d71953d62b1ba
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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