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

HRID 2071272Notes

Reaction equation

HRID 2071272 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-969bfcdd2996412d939878d4e01c8a55
Source dataset
uspto-grants-1977_09
Patent number
US04046767

Reaction notes

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