Methyl iodide → 4-(4-(Dimethylamino)-3-fluorophenyl)-1-methylpyridinium iodide

HRID 240227Notes

Reaction equation

HRID 240227 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][C:3]=1[N:4]([CH3:6])[CH3:5].[CH3:17][I:18]>C(#N)C>[I-:18].[CH3:6][N:4]([CH3:5])[C:3]1[CH:7]=[CH:8][C:9]([C:11]2[CH:12]=[CH:13][N+:14]([CH3:17])=[CH:15][CH:16]=2)=[CH:10][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 672021852-Fluoro-N,N-dimethyl-4-(pyridin-4-yl)aniline

Product 1

HCID 672001664-(4-(Dimethylamino)-3-fluorophenyl)-1-methylpyridinium iodideYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Fluoro-N,N-dimethyl-4-(pyridin-4-yl)aniline (0.5 g, 2.3 mmols) was dissolved in acetonitrile (50 ml) and methyl iodide (3 ml) was added. The mixture was heated at reflux for 2 hrs. This was cooled to ambient temperature and evaporated the product was purified by recrystallization from ethanol/diethyl ether. To give 0.2 g of 4-(4-(dimethylamino)-3-fluorophenyl)-1-methylpyridinium iodide 21% yield as a red solid. 1H NMR (DMSO-d6) δ 3.0 (s, 6H), 4.25 (s, 3H), 7.02 (t, 1H), 7.90 (m, 2H), 8.90 (d, 2H), 8.90 (d, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hrs
  3. customevaporated the product
  4. customwas purified by recrystallization from ethanol/diethyl ether

Sources & evidence

ORD record
ord-b4e79e0d5c7f4c46917d9fa75fc7a2ab
Source dataset
uspto-grants-2014_02
Patent number
US08647827B2

Reaction notes

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