Dimethyl Sulfate → 1-Methylquinolin-1-ium methyl sulfate

HRID 1731607Notes

Reaction equation

HRID 1731607 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:11][O:12][S:13]([O:16]C)(=[O:15])=[O:14]>C1C=CC=CC=1>[CH3:11][O:12][S:13]([O-:16])(=[O:15])=[O:14].[CH3:11][N+:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6497Dimethyl Sulfate2×HCID 7047Quinoline2×

Product 1

HCID 123341791-Methylquinolin-1-ium methyl sulfate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

Pure, commercial grades of quinoline, benzene and dimethylsulfate were stored over Molecular Sieve 4A for two days prior to reaction. Into a three liter, three-necked round bottomed flask fitted with an electrical heater, stirrer, dropping funnel and an efficient reflux condenser equipped with calcium chloride drying tube were placed quinoline 300 ml. (328.8 g., 2.54 moles) in benzene 900 ml. Dimethyl sulfate 240 ml. (319.2 g., 2.53 moles) in benzene 180 ml. was run in rapidly over five minutes while the contents were vigorously stirred. Spontaneous warming and refluxing occurred and the liquid separated into two phases. After the initial reaction had subsided the flask was heated to reflux for two hours and then allowed to cool for two hours. All the time the reagents were vigorously stirred until the cooled mixture became a suspension of small particles. These were filtered as far as removing Cthe solvent, washed with benzene 1000 ml. and refiltered, and were transferred to tared bottles in a vacuum desiccator over sulfuric acid and sodium hydroxide. The desiccator was evacuated at room temperature for about six hours when no further benzene was collected in a liquid nitrogen trap. Total yield of dried material 633.5 g. (98%).

Workup

  1. customto reaction
  2. customInto a three liter, three-necked round bottomed flask fitted with an electrical heater, stirrer
  3. customequipped with calcium chloride drying tube
  4. customrapidly over five minutes
  5. temperatureSpontaneous warming
  6. temperaturerefluxing
  7. customthe liquid separated into two phases
  8. customAfter the initial reaction
  9. temperaturewas heated
  10. temperatureto reflux for two hours
  11. temperatureto cool for two hours
  12. stirringAll the time the reagents were vigorously stirred until the cooled mixture
  13. additiona suspension of small particles
  14. filtrationThese were filtered as far
  15. customas removing Cthe solvent
  16. washwashed with benzene 1000 ml
  17. customThe desiccator was evacuated at room temperature for about six hours when no further benzene
  18. customwas collected in a liquid nitrogen trap

Sources & evidence

ORD record
ord-f098130203a24d42a61ea3b5f92b3da6
Source dataset
uspto-grants-1986_11
Patent number
US04622400

Reaction notes

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