Methyl iodide → 1,4-Dimethylpyridin-1-ium iodide

HRID 1416337Notes

Reaction equation

HRID 1416337 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[CH3:8][I:9]>C1(C)C=CC=CC=1>[I-:9].[CH3:7][C:4]1[CH:5]=[CH:6][N+:1]([CH3:8])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 79634-Methylpyridine

Product 1

HCID 2006031,4-Dimethylpyridin-1-ium iodide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 500 ml three-neck flask, fitted with a stirrer, thermometer, and condenser, was charged with 9.3 g (0.1 mol) of 4-picoline and 21.6 g (0.11 mol) of methyl iodide in toluene. The solution was stirred at room temperature for 4 hours, and then refluxed for 30 minutes. After cooling, the solution was filtered, and the pale yellow solid, 4-methyl-N-methylpyridinium iodide, was washed with ethyl ether and dried under vacuum. Yield 21.2 g (90%); 1H-NMR (DMSO-d6): δ2.56 (s, 3H), 4.20 (s, 3H), 7.0 (d, 2H), 8.90 (d, 2H) ppm.

Workup

  1. customA 500 ml three-neck flask, fitted with a stirrer
  2. temperaturerefluxed for 30 minutes
  3. temperatureAfter cooling
  4. filtrationthe solution was filtered
  5. washthe pale yellow solid, 4-methyl-N-methylpyridinium iodide, was washed with ethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-928b9c6f22f94037959732b37f422ade
Source dataset
uspto-grants-1999_06
Patent number
US05912257

Reaction notes

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