Hydrochloric Acid → 7-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

HRID 600861Notes

Reaction equation

HRID 600861 reaction equation
[F:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:18]([O:20]CC)=[O:19])=[CH:8][N:9]2[C@@H:14]2[CH2:16][C@@H:15]2[F:17])=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[F:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:18]([OH:20])=[O:19])=[CH:8][N:9]2[C@@H:14]2[CH2:16][C@@H:15]2[F:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12082408ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate

Product 1

HCID 120824067-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

After dissolving ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (34.0 g, 105 mmol) in acetic acid (400 ml) and then adding concentrated hydrochloric acid (400 ml) thereto, it was heated under reflux for 3 hours. After cooling, the reaction solution was poured into ice water (1500 ml), and the precipitated crystals were filtered out. After washing the filtered-out crystals with an excess amount of water, it was washed with cold ethanol and diethyl ether in that order, and after drying under a reduced pressure, the crude crystals obtained were purified by recrystallization from a mixed solvent of acetonitrile-ethanol and then dried under a reduced pressure. 27.1 g (87.4%) of the title compound was there by obtained in the form of a white powder.

Workup

  1. temperatureit was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals were filtered out
  5. washAfter washing the filtered-out crystals with an excess amount of water, it
  6. washwas washed with cold ethanol and diethyl ether in that order
  7. customafter drying under a reduced pressure
  8. customthe crude crystals obtained
  9. customwere purified by recrystallization from a mixed solvent of acetonitrile-ethanol
  10. customdried under a reduced pressure
  11. customby obtained in the form of a white powder

Sources & evidence

ORD record
ord-aa2c325d32354fecb200d3446c4c5d9a
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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