Methyl iodide → 1-Methyl-3-(2-methyl-1,3-dioxolan-2-yl)pyridinium iodide

HRID 2413025Notes

Reaction equation

HRID 2413025 reaction equation
[CH3:1][C:2]1([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[O:6][CH2:5][CH2:4][O:3]1.[CH3:13][I:14]>C1(C)C=CC=CC=1>[I-:14].[CH3:13][N+:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:2]2([CH3:1])[O:3][CH2:4][CH2:5][O:6]2)[CH:8]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 2807153-(2-Methyl-1,3-dioxolan-2-yl)pyridine

Product 1

HCID 133657531-Methyl-3-(2-methyl-1,3-dioxolan-2-yl)pyridinium iodideYield 99.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 3-l. three-necked flask, equipped with mechanical stirrer, reflux condenser and thermometer was charged under nitrogen with 155 g of 3-(2-methyl-1,3-dioxolan-2-yl)pyridine and 1.2 l of toluene. 272 g of methyl iodide was added. The mixture was stirred and heated at 53° (internal temp.) for 32 hours and then let stand at room temperature overnight. The precipitate was collected by filtration, washed with 500 ml of toluene, 500 ml of hexane and dried (r.t., 0.1 mm, const. weight) to yield 286.2 g (99.3%) of 1-methyl-3-(2-methyl-1,3-dioxolan-2-yl)pyridinium iodide as light yellow crystals, m.p. 185.5°-187° (sinters at 167°).

Workup

  1. customthree-necked flask, equipped with mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureheated at 53° (internal temp.) for 32 hours
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with 500 ml of toluene, 500 ml of hexane
  6. customdried (r.t., 0.1 mm, const. weight)

Sources & evidence

ORD record
ord-86d32adbfdc343239b2146d47a9c011a
Source dataset
uspto-grants-1985_01
Patent number
US04495354

Reaction notes

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