Ethanol → HCID 14651162, compound

HRID 232686Notes

Reaction equation

HRID 232686 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([CH3:18])=[C:16]3[C:11]([C:12](=[O:27])[C:13]([C:22]([O:24]CC)=[O:23])=[CH:14][N:15]3[CH:19]3[CH2:21][CH2:20]3)=[C:10]([CH3:28])[C:9]=2[F:29])[CH2:4][CH2:3]1.[OH-].[Na+].C(O)C>O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([CH3:18])=[C:16]3[C:11]([C:12](=[O:27])[C:13]([C:22]([OH:24])=[O:23])=[CH:14][N:15]3[CH:19]3[CH2:20][CH2:21]3)=[C:10]([CH3:28])[C:9]=2[F:29])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14651161HCID 14651161, compound

Product 1

HCID 14651162HCID 14651162, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethyl 7-(4-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-5, 8-dimethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (25 mg) are added 10% aqueous solution of sodium hydroxide (3 ml) and ethanol (3 ml), and the mixture is refluxed for 1 hour. After cooling, the reaction mixture is diluted with water and washed with dichloromethane. The aqueous layer is made acidic with acetic acid and then made weak alkaline with an aqueous sodium hydrogen carbonate. The resultant is extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure and to the residue is added diethyl ether. The precipitated crystals are filtered and recrystallized from ethanol to give 7-(4-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-5, 8-dimethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (14 mg), as yellow crystals, m.p. 205°-206° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. temperatureAfter cooling
  3. washwashed with dichloromethane
  4. extractionThe resultant is extracted with dichloromethane
  5. customthe extract is dried
  6. distillationThe solvent is distilled off under reduced pressure and to the residue
  7. additionis added diethyl ether
  8. filtrationThe precipitated crystals are filtered
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-31c409e89b2f48159c1ad8835025eca8
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Reaction notes

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