Methyl iodide → 4-[4-(Dimethylamino)phenyl]-1-methylpyridin-1-ium iodide

HRID 240219Notes

Reaction equation

HRID 240219 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:16][I:17]>C(#N)C>[I-:17].[CH3:1][N:2]([CH3:15])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][N+:12]([CH3:16])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 227783Pyridine, 4-(4-dimethylaminophenyl)-

Product 1

HCID 132272704-[4-(Dimethylamino)phenyl]-1-methylpyridin-1-ium iodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-dimethyl-4-(pyridine-4-yl)aniline (0.15 g, 7.6 mmols) was dissolved in acetonitrile (50 ml) and methyl iodide (4 ml) was added. The mixture was heated at reflux for 4 hrs then cooled to ambient temperature. IDT307 (0.17 g, 5 mmols) crystallized upon standing and was removed via filtration. 1H NMR (DMSO-d6) δ 3.40 (s, 6H), 4.25 (s, 3H), 6.92 (d, 2H), 8.06 (d, 2H), 8.38 (d, 2H), 8.80 (d, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hrs
  3. customIDT307 (0.17 g, 5 mmols) crystallized
  4. customwas removed via filtration

Sources & evidence

ORD record
ord-a35eba22304a40beb12a5a0dfb6f00a9
Source dataset
uspto-grants-2014_02
Patent number
US08647827B2

Reaction notes

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