Acetic Acid → 1-[(1R,2S)-2-Fluorocyclopropyl]-6,7,8-trifluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 1939268Notes

Reaction equation

HRID 1939268 reaction equation
[F:1][C@H:2]1[CH2:4][C@H:3]1[N:5]1[C:14]2[C:9](=[C:10]([CH3:18])[C:11]([F:17])=[C:12]([F:16])[C:13]=2[F:15])[C:8](=[O:19])[C:7]([C:20]([O:22]CC)=[O:21])=[CH:6]1.Cl.C(O)(=O)C>O>[F:1][C@H:2]1[CH2:4][C@H:3]1[N:5]1[C:14]2[C:9](=[C:10]([CH3:18])[C:11]([F:17])=[C:12]([F:16])[C:13]=2[F:15])[C:8](=[O:19])[C:7]([C:20]([OH:22])=[O:21])=[CH:6]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 70250897Ethyl 1-[(1R,2S)-2-Fluorocyclopropyl]-6,7,8-trifluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 228799641-[(1R,2S)-2-Fluorocyclopropyl]-6,7,8-trifluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidYield 104.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.00 g of ethyl 1-[-(1R,2S)-2-fluorocyclopropyl]-6,7,8-trifluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate, 10 ml of concentrated hydrochloric acid, and 20 ml of acetic acid was heated under reflux for 1 hour and, after allowing to cool, water was added thereto. The precipitated crystals were collected by filtration, washed with water and ethanol, and dried to yield 960 mg of the titled compound as a pale yellow powderous crystal, which was then recrystallized from a mixed solvent of ethanol and chloroform.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureto cool
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with water and ethanol
  6. customdried

Sources & evidence

ORD record
ord-d8d0b97759ca4560a5e41968db5fa48c
Source dataset
uspto-grants-1997_12
Patent number
US05696132

Reaction notes

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