N-Pyridin-4-ylacetamide → 1-[2-(3,4-Dimethoxyphenyl)ethyl]-4-acetamidopyridinium iodide

HRID 1730325Notes

Reaction equation

HRID 1730325 reaction equation
[I:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1.[C:14]([NH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)(=[O:16])[CH3:15]>C(O)C>[I-:1].[CH3:13][O:12][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][N+:21]2[CH:22]=[CH:23][C:18]([NH:17][C:14](=[O:16])[CH3:15])=[CH:19][CH:20]=2)[CH:9]=[CH:8][C:7]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 21288N-Pyridin-4-ylacetamideHCID 5970224-(2-Iodoethyl)-1,2-dimethoxybenzene

Product 1

HCID 214132591-[2-(3,4-Dimethoxyphenyl)ethyl]-4-acetamidopyridinium iodideYield 67.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Iodoethyl)-3,4-dimethoxybenzene (29.3 g.) and 4-acetamidopyridine (14.0 g.) in absolute ethanol (100 ml.) were refluxed for 2.5 hours. The resulting crystalline material was collected and recrystallised from ethanol to give the title compound (29.1 g.), m.p. 201°-202°C. (Found: C, 47.9; H, 4.9; N, 6.3; C17H21IN2O3 requires C, 47.7; H, 4.9; N, 6.5%).

Workup

  1. customThe resulting crystalline material was collected
  2. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-3b203e8f655b45ceb642ad9772d2a559
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

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