Potassium Cyanide → 2-(quinolin-2-yl)acetonitrile

HRID 1819781Notes

Reaction equation

HRID 1819781 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.C([O-])(O)=O.[Na+].[C-:19]#[N:20].[K+]>CCO.O>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][C:19]#[N:20]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 2643022-(quinolin-2-yl)acetonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-Chloromethyl-quinoline hydrochloride (TCI, 4.28 g, 20 mmol) in 50 mL of EtOH was added a solution of NaHCO3 (EM, 3.36 g, 40 mmol) in 30 mL of H2O. The mixture was stirred for 15 min, then was added KI (Aldrich, 4.5 g, 30 mmol) and KCN (Acros, 1.95 g, 30 mmol) and the resulting mixture was refluxed for 4 h. after cooled to room temperature, EtOH was removed under reduced pressure. The residue was extracted 3× with EtOAc (200 mL). The organic layers were combined and washed twice with a brine solution (200 mL), dried over Na2SO4, and concentrated under vacuum. The residue was chromatographed (30% EtOAc/hexanes) to yield 2.76 g (82%) of product. 1H NMR (400 MHz, DMSO-d6) δ 8.42 (d, J=8.4 Hz, 1H), 8.05-7.97 (m, 2H), 7.85-7.76 (m, 1H), 7.67-7.60 (m, 1H), 7.54 (d, J=8.5 Hz, 1H), 4.45 (s, 2H). MS (EI): m/z 169 (M+H).

Workup

  1. temperaturethe resulting mixture was refluxed for 4 h.
  2. customEtOH was removed under reduced pressure
  3. extractionThe residue was extracted 3× with EtOAc (200 mL)
  4. washwashed twice with a brine solution (200 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was chromatographed (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-114a36dff4424f02b2f1a942050f5ed6
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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