Hydrochloric Acid → 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-4-oxoquinoline-3-Carboxylic Acid

HRID 600866Notes

Reaction equation

HRID 600866 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:16]([O:18]CC)=[O:17])=[CH:8][N:9]2[C@@H:12]2[CH2:14][C@@H:13]2[F:15])=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:16]([OH:18])=[O:17])=[CH:8][N:9]2[C@@H:12]2[CH2:14][C@@H:13]2[F:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67271230ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 672714987-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-4-oxoquinoline-3-Carboxylic AcidYield 95.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylate (4.08 g, 13.9 mmol), acetic acid (9 ml) and concentrated hydrochloric acid (9 ml) was heated under reflux for 21 hour. After cooling the reaction solution with ice, ice water (50 ml) was poured into the reaction solution, the precipitated crystals were filtered out, and after washing with excess water, a small amount of cold ethanol and excess diethyl ether, the crystals were dried under a reduced pressure at 80° C. for 16 hours. 3.51 g (95%) of the title compound was thereby obtained in the form of a white powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 21 hour
  3. additionwas poured into the reaction solution
  4. filtrationthe precipitated crystals were filtered out
  5. washafter washing with excess water
  6. dry with materiala small amount of cold ethanol and excess diethyl ether, the crystals were dried under a reduced pressure at 80° C. for 16 hours

Sources & evidence

ORD record
ord-27ba94ab08534ceabd497bb598066fc4
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

Loading…