Potassium Cyanide → 2-Naphthylacetonitrile

HRID 619347Notes

Reaction equation

HRID 619347 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[C-:13]#[N:14].[K+]>CN(C=O)C>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH2:2][C:13]#[N:14]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 703202-Bromomethylnaphthalene

Product 1

HCID 820082-NaphthylacetonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromomethyinaphthalene (5.00 g, 23 mmol) was dissolved in N,N'-dimethylformamide (50 ml) and potassium cyanide (2.95 g, 45 mmol) was added and the resulting mixture was stirred at room temperature for 16 hours. The supernatant was decanted and partitioned between water (100 ml) and diethyl ether (2×75 ml). The combined organic phases were washed with water (100 ml), dried (MgSO4), filtered and evaporated in vacuo affording 2.53 g (67%) of 2-naphtylacetonitrile as a solid.

Workup

  1. customThe supernatant was decanted
  2. custompartitioned between water (100 ml) and diethyl ether (2×75 ml)
  3. washThe combined organic phases were washed with water (100 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-0afab0dcea0f40ac91b27ad2d7347690
Source dataset
uspto-grants-1999_09
Patent number
US05958957

Reaction notes

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