Hydrochloric Acid → HCID 19072247, compound

HRID 1955763Notes

Reaction equation

HRID 1955763 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:22])=[C:11]([C:16]4(O)[CH2:18][C:17]4=C=O)[C:12]=3[O:14][CH3:15])[C:7](=[O:23])[C:6]([C:24]([O:26]CC)=[O:25])=[CH:5]2)[CH2:3][CH2:2]1.[OH-:29].[Na+].Cl.[CH2:32]([OH:34])C>>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:22])=[C:11]([C:16]4([C:32]([OH:34])=[O:29])[CH2:17][CH2:18]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:23])[C:6]([C:24]([OH:26])=[O:25])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86752892HCID 86752892, compound

Product 1

HCID 19072247HCID 19072247, compoundYield 86.2%

Procedure

180 mg of ethyl 1-cyclopropyl-6-fluoro-7-(1-hydroxy-carbonylcyclopropyl)-8-methoxy-1,4-dihydro-4-oxo-3-quino-linecarboxylate was suspended in 2 ml of ethanol. After adding 1 ml of 2N NaOH, the mixture was stirred at room temperature for 15 hours. Then 2N HCl was added to the reaction mixture and the organic layer was collected, successively washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the residue was crystallized from diisopropyl ether and the crystals were collected by filtration. Thus 144 mg of 1-cyclopropyl-6-fluoro-7-(1-hydroxycarbonylcyclopropyl)-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was obtained (yield: 86.2%).

Workup

  1. customthe organic layer was collected
  2. washsuccessively washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  4. customAfter removing the solvent under reduced pressure
  5. customthe residue was crystallized from diisopropyl ether
  6. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-cba18e42d7e744369f72d4a77a9cbbaa
Source dataset
uspto-grants-1998_07
Patent number
US05776948

Reaction notes

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