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

HRID 1911862Notes

Reaction equation

HRID 1911862 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].[CH3:8][N+:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 79634-Methylpyridine

Product 1

HCID 2006031,4-Dimethylpyridin-1-ium iodideYield 67.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-picoline (18.6 g, 0.2 mol) in toluene (100 mL), methyl iodide (56.8 g, 0.4 mol) was added dropwise at room temperature. After the addition, the mixture was stirred at room temperature for 5 hrs. The precipitate was collected by filtration, washed with toluene and dried under vacuum to give Compound 7 as an off-white solid (31.6 g, 67%). The structure of Compound 7 is given below:

Workup

  1. additionAfter the addition
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with toluene
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5ab71f0c6b6f4c3e84c0ac06846cb5ac
Source dataset
uspto-grants-2013_12
Patent number
US08604204B2

Reaction notes

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