Dimethyl Sulfate → HCID 22250101, compound

HRID 412053Notes

Reaction equation

HRID 412053 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 22250101HCID 22250101, compound

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-91feee2a353b4c45ad27e03f334cc15a
Source dataset
uspto-grants-2003_05
Patent number
US06562838B2

Reaction notes

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