Methyl iodide → 2-(2-Furoyl)-1,4-dimethylpyridinium iodide

HRID 46533Notes

Reaction equation

HRID 46533 reaction equation
[CH3:1][I:2].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=1)=[O:9]>C1(C)C=CC=CC=1.CC(C)=O>[I-:2].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N+:11]=1[CH3:1])=[O:9]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 203875722-(2-Furoyl)-4-methylpyridine

Product 1

HCID 203875702-(2-Furoyl)-1,4-dimethylpyridinium iodideYield 84%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

49.7 gr of methyl iodide dissolved in 43 ml of anhydrous toluene are added to a solution of 5.5 gr of 2-(2-furoyl)-4-methylpyridine in 35.5 ml of anhydrous acetone. The mixture is kept under reflux for ninety-six hours. Following this, it is cooled for twelve hours. 8.1 g (Yield: 84%) of 2-(2-furoyl)-1,4-dimethylpyridinium iodide (I) with a melting point of 190°-95° C. are removed by filtering. An analytical sample recrystallized from ethanol has a melting point of 202-3° C. Analysis calculated for C12H12NO2I: C: 43.78; H: 3.67; N: 4.25. Found: 43.76; H: 3.73; N: 4.50.

Workup

  1. temperatureunder reflux for ninety-six hours
  2. temperatureis cooled for twelve hours

Sources & evidence

ORD record
ord-b4aa51d97ef44affbfd23a9b59453e40
Source dataset
uspto-grants-1979_11
Patent number
US04173705

Reaction notes

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