2-Chloropyridine → alpha-Phenyl-2-pyridineacetonitrile

HRID 1107430Notes

Reaction equation

HRID 1107430 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:15]#[N:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-])C.[K+]>CN(C=O)C>[C:9]1([CH:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[C:15]#[N:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 79772-ChloropyridineHCID 8794PhenylacetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 95510alpha-Phenyl-2-pyridineacetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) solution of 2-chloropyridine (4.8 mL, 50 mmol) and benzyl cyanide (5.8 ml, 50 mmol) in 120 ml of DMF, was added with potassium t-butoxide (11.2 g, 100 mmol), under N2. The reaction mixture was reacted for 3 hours and then partitioned between EtOAc and H2O. The resulting layers were separated and the EtOAc layer was washed sequentially with NaHCO3 and brine, dried over Na3SO4, filtered and concentrated in vacuo. The crude material was purified by recrystallization (hexanes/EtOAc).

Workup

  1. customThe reaction mixture was reacted for 3 hours
  2. custompartitioned between EtOAc and H2O
  3. customThe resulting layers were separated
  4. washthe EtOAc layer was washed sequentially with NaHCO3 and brine
  5. dry with materialdried over Na3SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by recrystallization (hexanes/EtOAc)

Sources & evidence

ORD record
ord-7d94a4378819435a8d1795e8003456e9
Source dataset
uspto-grants-2000_05
Patent number
US06060484

Reaction notes

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