Methyl iodide → HCID 67200828, compound

HRID 240224Notes

Reaction equation

HRID 240224 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:5]([CH3:15])[CH:4]=1.[CH3:17][I:18]>C(#N)C>[I-:18].[CH3:1][N:2]([CH3:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N+:12]([CH3:17])=[CH:11][CH:10]=2)=[C:5]([CH3:15])[CH:4]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 13231099N,N,3-Trimethyl-4-(pyridin-4-yl)aniline

Product 1

HCID 67200828HCID 67200828, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N,3-trimethyl-4-(pyridine-4-yl)aniline (0.2 g, 0.9 mmols) was dissolved in acetonitrile (50 ml) and methyl iodide (3 ml) was added. The mixture was heated at reflux with stirring for 2 hrs cooled and evaporated to a volume of 10 ml. Then diethyl ether (50 ml) was added and the product crystallized resulting in (0.068 g, 0.19 mmols) of 4-(4-(dimethylamino)-2-methylphenyl)-1-methylpyridinium iodide as a red solid. 1H NMR (DMSO-d6) δ 2.40 (s, 3H), 3.00 (s, 6H), 4.30 (s, 3H), 6.70 (m, 2H), 6.90 (d, 2H), 8.10 (d, 2H), 8.85 (d, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. temperaturecooled
  4. customevaporated to a volume of 10 ml
  5. additionThen diethyl ether (50 ml) was added
  6. customthe product crystallized

Sources & evidence

ORD record
ord-6c8f188474c74a7ba33b34f34d276a01
Source dataset
uspto-grants-2014_02
Patent number
US08647827B2

Reaction notes

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