Sodium Cyanide → 6-Benzyloxyindole-3-acetonitrile

HRID 37942Notes

Reaction equation

HRID 37942 reaction equation
[I-].[CH2:2]([O:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH2:19][N+](C)(C)C)=[CH:15][NH:16]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C-:24]#[N:25].[Na+]>CCO>[CH2:2]([O:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH2:19][C:24]#[N:25])=[CH:15][NH:16]2)=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86590995(6-benzyloxy-1H-indol-3-ylmethyl)-trimethylammonium iodide

Product 1

HCID 40714386-Benzyloxyindole-3-acetonitrileYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (6-benzyloxy-1H-indol-3-ylmethyl)-trimethylammonium iodide (2.2 g, 5 mmol), sodium cyanide (500 mg, 10.2 mmol), and 95% EtOH (50 mL) was refluxed under nitrogen for 5 hours. The solvent was removed in vacuo, and the residue was taken in DCM, and washed with water, then dried with sodium sulfate, and evaporated in vacuo to afford a white solid, which was recrystallized from EtOH to give (6-benzyloxy-1H-indol-3-yl)-acetonitrile (1.25 g, 86%). MS (ES): 263 (MH+).

Workup

  1. temperaturewas refluxed under nitrogen for 5 hours
  2. customThe solvent was removed in vacuo
  3. washwashed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated in vacuo
  6. customto afford a white solid, which
  7. customwas recrystallized from EtOH

Sources & evidence

ORD record
ord-ecdd8730bf054addaf19f6bed219d9fa
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

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