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

HRID 1607572Notes

Reaction equation

HRID 1607572 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-3dc746281446420b811b1843345897d2
Source dataset
uspto-grants-1989_09
Patent number
US04866077

Reaction notes

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