Acetic Acid → 6,7-Difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 1939270Notes

Reaction equation

HRID 1939270 reaction equation
[F:1][C:2]1[C:3]([CH3:23])=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]([C@@H:13]1[CH2:15][C@@H:14]1[F:16])[CH:7]=[C:6]([C:17]([O:19]CC)=[O:18])[C:5]2=[O:22].Cl.C(O)(=O)C>O>[F:1][C:2]1[C:3]([CH3:23])=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]([C@@H:13]1[CH2:15][C@@H:14]1[F:16])[CH:7]=[C:6]([C:17]([OH:19])=[O:18])[C:5]2=[O:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 70250922Ethyl 6,7-Difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 228799656,7-Difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidYield 63.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.70 g of ethyl 6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate, 30 ml of concentrated hydrochloric acid, and 60 ml of acetic acid was heated under reflux for 1.5 hours. After allowing to cool, water was added to the reaction mixture. The precipitated crystals were collected by filtration, washed with water and ethanol, and dried. Recrystallization from a mixed solvent of ethanol and chloroform yielded 990 mg of the titled compound as a pale yellow powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureto cool
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with water and ethanol
  6. customdried
  7. customRecrystallization from a mixed solvent of ethanol and chloroform

Sources & evidence

ORD record
ord-9092e2369ce04aeca8054644f9ebb00b
Source dataset
uspto-grants-1997_12
Patent number
US05696132

Reaction notes

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