Methyl iodide → 4-(Methoxycarbonyl)-1-methylpyridin-1-ium iodide

HRID 2236847Notes

Reaction equation

HRID 2236847 reaction equation
[C:1]([O:9][CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[I:11][CH3:12]>C1C=CC=CC=1>[I-:11].[CH3:10][O:9][C:1]([C:2]1[CH:7]=[CH:6][N+:5]([CH3:12])=[CH:4][CH:3]=1)=[O:8]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 227085Methyl isonicotinate

Product 1

HCID 129454874-(Methoxycarbonyl)-1-methylpyridin-1-ium iodideYield 46%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of methyl isonicotinate (5.0 g, 36 mmol) in benzene (165 mL) is added iodomethane (4.5 mL, 72 mmol). The mixture is heated in a 110° C. oil bath for two hours and then allowed to cool to room temperature. The solid is collected by Büchner filtration, washed with hexanes and diethyl ether, and dried under house vacuum to give 4-methoxycarbonyl-1-methylpyridinium iodide (4.6 g, 46%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe solid is collected by Büchner filtration
  3. washwashed with hexanes and diethyl ether
  4. customdried under house vacuum

Sources & evidence

ORD record
ord-e2cfd27a3cc549d4a7098ed6ac9adefa
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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