Dimethyl Sulfate → Quinolinium, 1,2-dimethyl-, methyl sulfate (1:1)

HRID 1241685Notes

Reaction equation

HRID 1241685 reaction equation
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]=1[CH3:3].[S:12]([O:17]C)([O:15][CH3:16])(=[O:14])=[O:13]>>[CH3:16][O:15][S:12]([O-:17])(=[O:14])=[O:13].[CH3:16][N+:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]=1[CH3:3]

Participants

3

Reactant 2

HCID 6497Dimethyl SulfateHCID 70602-Methylquinoline

Product 1

HCID 197744Quinolinium, 1,2-dimethyl-, methyl sulfate (1:1)Yield 181.9%

Conditions

Temperature
100 °C

Procedure

(Method C) (Quinaldinium methyl sulphate salts) Quinaldine (6 g, 41.9 mmol) and dimethyl sulphate (5.28 g, 41.9 mmol, 1 eq) were mixed and heated on a 100° C. oil bath for 5 mins giving a yellow solid. The crude product was recrystallised by dissolving in the minimum amount of methanol at reflux, allowing to cool slightly, precipitating with diethyl ether, cooling, filtering and drying to give the title compound (10.27 g, 38.1 mmol, 91%).

Workup

  1. customgiving a yellow solid
  2. customThe crude product was recrystallised
  3. dissolutionby dissolving in the minimum amount of methanol
  4. temperatureat reflux
  5. temperatureto cool slightly
  6. customprecipitating with diethyl ether
  7. temperaturecooling
  8. filtrationfiltering
  9. customdrying

Sources & evidence

ORD record
ord-a7f02ba54abd48dfad89c7c98e474f91
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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