Dimethyl Sulfate → Ethyl 7-fluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1722247Notes

Reaction equation

HRID 1722247 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:17])=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:18](=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:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][N:9]2[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178469609Ethyl 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 22250101Ethyl 7-fluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of ethyl 7-fluoro-4-hydroxyquinoline-3-carboxylate (4.7 g), anhydrous potassium carbonate (3.0 g), dimethyl sulphate (2.52 g) and butanone (200 ml) was boiled under reflux for 14 hours. The solvent was evaporated and the residue was triturated with dichloromethane (150 ml). The mixture was filtered and the filtrate was evaporated to a small volume. Diethyl ether was added, causing a solid to precipitate. The solid was collected, washed with ether, dried and recrystallised from IMS to give the novel compound ethyl 7-fluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate, m.p. 164°-166°.

Workup

  1. temperatureunder reflux for 14 hours
  2. customThe solvent was evaporated
  3. customthe residue was triturated with dichloromethane (150 ml)
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated to a small volume
  6. additionDiethyl ether was added
  7. customto precipitate
  8. customThe solid was collected
  9. washwashed with ether
  10. customdried
  11. customrecrystallised from IMS

Sources & evidence

ORD record
ord-3f75340911514b1095ce7204187fa45a
Source dataset
uspto-grants-1989_08
Patent number
US04855291

Reaction notes

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