Sodium hydride → Fluoroquinolonic acid

HRID 637925Notes

Reaction equation

HRID 637925 reaction equation
[H-].[Na+].Cl[C:4]1[CH:22]=[C:21]([Cl:23])[C:20]([F:24])=[CH:19][C:5]=1[C:6]([C:8](=[CH:14][NH:15][CH:16]1[CH2:18][CH2:17]1)[C:9]([O:11]CC)=[O:10])=[O:7]>O1CCOCC1.O>[Cl:23][C:21]1[CH:22]=[C:4]2[C:5]([C:6](=[O:7])[C:8]([C:9]([OH:11])=[O:10])=[CH:14][N:15]2[CH:16]2[CH2:18][CH2:17]2)=[CH:19][C:20]=1[F:24]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 178471868HCID 178471868, compound

Product 1

HCID 483180Fluoroquinolonic acidYield 106.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

3.44 g of 80 percent strength sodium hydride are added in portions to a stirred ice-cooled solution of 31.9 g of ethyl 2-(2,4-dichloro-5-fluoro-benzoyl)-3-cyclopropylamino-acrylate (6) in 100 ml of anhydrous dioxane. Thereafter, the mixture is stirred for 30 minutes at room temperature and for 2 hours under reflux, and the dioxane is stripped off in vacuo. The residue (40.3 g) is suspended in 150 ml of water, 6.65 g of caustic alkali are added and the mixture is refluxed for 1.5 hours. The warm solution is filtered, and the residue is rinsed with H2O. The ice-cooled filtrate is then acidified to pH=1-2 with semi-concentrated hydrochloric acid, and the precipitate is filtered off under suction, washed with water and dried in vacuo at 100° C. In this manner, 27.7 g of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid Via of melting point 234°-237° C. are obtained.

Workup

  1. temperatureunder reflux
  2. addition6.65 g of caustic alkali are added
  3. temperaturethe mixture is refluxed for 1.5 hours
  4. filtrationThe warm solution is filtered
  5. washthe residue is rinsed with H2O
  6. temperatureThe ice-cooled filtrate
  7. filtrationthe precipitate is filtered off under suction
  8. washwashed with water
  9. customdried in vacuo at 100° C

Sources & evidence

ORD record
ord-c27cd06f76574650a0c54e14e084c690
Source dataset
uspto-grants-1985_12
Patent number
US04559341

Reaction notes

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