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

HRID 1280450Notes

Reaction equation

HRID 1280450 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) can be boiled under reflux for 14 hours. The solvent can be evaporated and the residue can be triturated with dichloromethane (150 ml). The mixture can be filtered and the filtrate evaporated to a small volume. Diethyl ether can be added, causing a solid to precipitate. The solid can be collected, washed with ether, dried and recrystallised from industrial methylated spirit to give the compound ethyl 7- fluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate, m.p. 164° C.-166° C.

Workup

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

Sources & evidence

ORD record
ord-f324fe1ef701451695c3ccee1c62ed23
Source dataset
uspto-grants-2002_09
Patent number
US06451813B1

Reaction notes

Loading…