Sodium Cyanide → (4-Methyl-1H-indol-3-yl)acetonitrile

HRID 868840Notes

Reaction equation

HRID 868840 reaction equation
[I-].C[N+](C)(C)[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[CH3:14])[NH:7][CH:6]=1.[C-:17]#[N:18].[Na+]>C(O)C>[CH3:14][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[C:5]([CH2:4][C:17]#[N:18])=[CH:6][NH:7]2

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86665673HCID 86665673, compound

Product 1

HCID 24905095(4-Methyl-1H-indol-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trimethyl-(4-methyl-1H-indol-3-ylmethyl)-ammonium iodide (2.6 g, 7.5 mmol) is suspended in ethanol (53 mL) and sodium cyanide (736 mg, 15 mmol), is added to the reaction. The reaction is stirred and heated to reflux overnight. After 16 hours the reaction is cooled to room temperature and evaporated in vacuo. The resulting oil is taken up in dichloromethane and washed with water 3×, dried (Na2SO4), filtered and evaporated in vacuo. The resulting material is purified on silica with hexanes/dichloromethane as the eluent (1.0 g, 5 mmol, 71%) LC/MS (M++1): 171.3.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customevaporated in vacuo
  4. washwashed with water 3×
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-5e89b2837b41477e8fc6b3747a7c97a7
Source dataset
uspto-grants-2015_03
Patent number
US08969348B2

Reaction notes

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