Hydrochloric Acid → 1-(5-Amino-6-chloropyridin-3-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 610199Notes

Reaction equation

HRID 610199 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:21])=[C:16]([F:20])[C:17]=3[Cl:19])[C:12](=[O:22])[C:11]([C:23]([O:25]CC)=[O:24])=[CH:10]2)[CH:5]=[N:6][C:7]=1[Cl:8].Cl>>[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:21])=[C:16]([F:20])[C:17]=3[Cl:19])[C:12](=[O:22])[C:11]([C:23]([OH:25])=[O:24])=[CH:10]2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 22121231Ethyl 1-(5-amino-6-chloropyridine-3-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 221212811-(5-Amino-6-chloropyridin-3-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 92.2%

Procedure

To 100 mg of ethyl 1-(5-amino-6-chloropyridin-3-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate was added 3 ml of concentrated hydrochloric acid, and the mixture was heated under reflux for 2 hours. The reaction solution was allowed to cool, and the solid precipitated was collected by filtration. The solid was washed with ethanol to obtain 86 mg of the title compound as a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. customthe solid precipitated
  5. filtrationwas collected by filtration
  6. washThe solid was washed with ethanol

Sources & evidence

ORD record
ord-00281d699deb4c7e883bd4e9a78f2315
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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