Hydrochloric Acid → 7-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 600859Notes

Reaction equation

HRID 600859 reaction equation
[F:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19]CC)=[O:18])=[CH:8][N:9]2[C@@H:13]2[CH2:15][C@@H:14]2[F:16])=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[F:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([OH:19])=[O:18])=[CH:8][N:9]2[C@@H:13]2[CH2:15][C@@H:14]2[F:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67271688Ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate

Product 1

HCID 577586807-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate (1.40 g, 4.56 mmol) was dissolved in acetic acid (4 ml), and after adding concentrated hydrochloric acid (4 ml) thereto, it was heated under reflux for 3 hours. After cooling, the reaction solution was poured into ice water (50 ml) and the precipitated crystals were filtered out. After washing the filtered-out crystals with an excess amount of water, washing in cold ethanol and washing in diethyl ether were performed in that order, and after drying under a reduced pressure, 1.18 g (93%) of the title compound was 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
  6. washwashing in cold ethanol
  7. washwashing in diethyl ether
  8. customafter drying under a reduced pressure

Sources & evidence

ORD record
ord-597121bfda5c4cbda520ef4b3f4906bc
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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