Methyl iodide → (3-hydroxypyridin-2-yl)-N,N,N-trimethylmethanaminium iodide

HRID 2389918Notes

Reaction equation

HRID 2389918 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][N:6]=1)[CH3:3].[I:12][CH3:13]>CC(C)=O>[I-:12].[OH:11][C:10]1[C:5]([CH2:4][N+:2]([CH3:13])([CH3:1])[CH3:3])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 751082-((Dimethylamino)methyl)pyridin-3-ol

Product 1

HCID 2777200(3-hydroxypyridin-2-yl)-N,N,N-trimethylmethanaminium iodideYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-[(dimethylamino)methyl]pyridin-3-ol (207 g, 1.37 mol) in acetone (2000 mL) was added dropwise iodomethane (778 g, 5.48 mol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The resulting crystals were collected by filtration to give the title compound (369 g, yield 92%).

Workup

  1. temperaturecooling
  2. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-284a51039d62448186ac07493290f9ad
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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