Dimethyl Sulfate → Flosequinan

HRID 1155520Notes

Reaction equation

HRID 1155520 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[CH:7]([S:12]([CH3:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(=O)CC>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([S:12]([CH3:14])=[O:13])=[CH:8][N:9]2[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 705794307-Fluoro-3-methylsulphinyl-4-quinolone

Product 1

HCID 4474062Flosequinan

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

7-Fluoro-3-methylsulphinyl-4-quinolone (5.0 g.) was dissolved in hot butanone (250 ml.) containing anhydrous potassium carbonate (3.06 g.). The resulting suspension was stirred and treated dropwise with dimethyl sulphate (2.09 ml.). The mixture was stirred and boiled under reflux for 1 hour and filtered while hot. The filtrate was allowed to cool, giving a crystalline product. The product was collected and dried to give 7-fluoro-1-methyl-3-methylsulphinyl-4-quinolone, m.p. 226°-8°.

Workup

  1. stirringThe mixture was stirred
  2. temperatureunder reflux for 1 hour
  3. filtrationfiltered while hot
  4. temperatureto cool
  5. customgiving a crystalline product
  6. customThe product was collected
  7. customdried

Sources & evidence

ORD record
ord-47a90ed0e75b4d17b3f3b5b5c34ac574
Source dataset
uspto-grants-1981_11
Patent number
US04302460

Reaction notes

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