Methyl iodide → 2-[2-(p-Methoxybenzamido)benzyl]-1-methylpyridinium iodide

HRID 461918Notes

Reaction equation

HRID 461918 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]1[CH:24]=[CH:23][CH:22]=[CH:21][C:9]=1[NH:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[CH3:25][I:26]>CC(C)=O>[I-:26].[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:10][C:9]2[CH:21]=[CH:22][CH:23]=[CH:24][C:8]=2[CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N+:1]=2[CH3:25])=[O:20])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 205599902'-(2-Pyridylmethyl)-p-anisanilide

Product 1

HCID 205600092-[2-(p-Methoxybenzamido)benzyl]-1-methylpyridinium iodideYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2'-(2-Pyridylmethyl)-p-anisanilide (9.5 g., 0.03 mole) and 0.3 mole of methyl iodide in 100 ml. of acetone is refluxed with stirring for a period of 64 hr. The reaction mixture filtered and the filter cake washed with acetone provides a 93% yield of 2-[2-(p-methoxybenzamido)-benzyl]-1-methylpyridinium iodide, m.p. 184°-186° C. (corr.).

Workup

  1. filtrationThe reaction mixture filtered
  2. washthe filter cake washed with acetone

Sources & evidence

ORD record
ord-1d050e6eb98f49b689aa4b6de2bdeab6
Source dataset
uspto-grants-1977_12
Patent number
US04064254

Reaction notes

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