Methyl iodide → 1,3,4-Trimethylpyridin-1-ium iodide

HRID 1707598Notes

Reaction equation

HRID 1707598 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:9][I:10]>CC(C)=O>[I-:10].[CH3:9][N+:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 114173,4-Dimethylpyridine

Product 1

HCID 125431661,3,4-Trimethylpyridin-1-ium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

As shown in Scheme 2 (in FIG. 2), a solution of 100 g of 3,4-dimethylpyridine in 800 ml of acetone was added dropwise to 57.27 mL of methyl iodide. The reaction mixture was stirred at room temperature for 18 hrs. The solid was collected by filtration and washed with cold ether. After drying under vacuum, there was obtained 202 g of 1,3,4-trimethylpyridinium iodide. The subsequent Grignard reaction was conducted under standard conditions to afford an unstable intermediate that was utilized immediately.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with cold ether
  3. customAfter drying under vacuum

Sources & evidence

ORD record
ord-ce38c26ff9634aa1870c0c0115da3771
Source dataset
uspto-grants-1994_10
Patent number
US05354758

Reaction notes

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