3-Cyanopyridine → 3-CYANO-1-METHYLPYRIDINIUM IODIDE

HRID 1650684Notes

Reaction equation

HRID 1650684 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[CH3:9][I:10]>CC(C)=O>[I-:10].[C:1]([C:3]1[CH:4]=[N+:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 793-CyanopyridineHCID 6328Methyl iodide2×

Product 1

HCID 112073273-CYANO-1-METHYLPYRIDINIUM IODIDEYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Cyanopyridine (1) (104 g, 1 mol) and methyl iodide (150 g, 1.06 mol) in acetone (500 ml) was stirred for 5 hours at room temperature. Then more methyl iodide (20 g, 0.14 mol) was added, and the reaction mixture was stirred overnight at room temperature. The mixture was filtered, and the solid product was washed with acetone (100 ml) and then thoroughly with ether. After drying, 199 g (0.81 mol, 81%) of the title compound were obtained, M.P. 145°-150° C.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid product was washed with acetone (100 ml)
  3. customAfter drying

Sources & evidence

ORD record
ord-fe0671aeedad43d9a9c23e18c48c0c20
Source dataset
uspto-grants-1990_05
Patent number
US04925858

Reaction notes

Loading…