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

HRID 1600437Notes

Reaction equation

HRID 1600437 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-52dda751726540faa13449f9467d216d
Source dataset
uspto-grants-1999_11
Patent number
USRE036374

Reaction notes

Loading…