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

HRID 1702984Notes

Reaction equation

HRID 1702984 reaction equation
[C:1]([O:9][CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:11][I:12]>CO>[I-:12].[CH3:10][O:9][C:1]([C:2]1[CH:7]=[CH:6][N+:5]([CH3:11])=[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 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

700 g of methyl isonicotinate and 1.4 kg of methyl iodide were admixed in 2.0 liters of methanol and the resultant solution was stirred and refluxed for 5 hours. After cooling, the mixture was filtered off and the product was washed with ether and dried to obtain 1.385 kg of 4-methoxycarbonyl-1-methylpyridinium iodide (97.2% yield).

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered off
  4. washthe product was washed with ether
  5. customdried

Sources & evidence

ORD record
ord-7233c854730d4f9eb2de66fb6d0e1e1a
Source dataset
uspto-grants-1982_09
Patent number
US04350697

Reaction notes

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