Potassium Cyanide → 2-(5-bromo-1H-indol-3-yl)acetonitrile

HRID 330279Notes

Reaction equation

HRID 330279 reaction equation
COS([O-])(=O)=O.[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][N+](C)(C)C.[C-:22]#[N:23].[K+]>O>[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][C:22]#[N:23]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 19869668(5-Bromo-3-indolylmethyl)-trimethylammonium Methyl Sulfate

Product 1

HCID 138059442-(5-bromo-1H-indol-3-yl)acetonitrileYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

According to the procedure of C. Huebner et al., J. Am. Chem. Soc., 75, 5887 (1953), (5-bromo-3-indolylmethyl)-trimethylammonium methyl sulfate (41.6 g, 0.11 mol) was added to a solution of potassium cyanide (21.49 g, 0.33 mol) in water (215 mL) and stirred at 60°-70° C. for 1 hour. The reaction was cooled to room temperature, extracted with ether (2×400 mL), washed with saturated NaHCO3, brine, dried (MgSO4), and concentrated under reduced pressure to yield 23.4 g (90%) of product as a white solid.

Workup

  1. extractionextracted with ether (2×400 mL)
  2. washwashed with saturated NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-233bf19a0dd245b192e04c39c69dc850
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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