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

HRID 437213Notes

Reaction equation

HRID 437213 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 collectd 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. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-12080977457145908188d689a8d8b499
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Reaction notes

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