Water → alpha-Phenyl-2-pyridineacetonitrile

HRID 1266236Notes

Reaction equation

HRID 1266236 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[NH2-].[Na+].O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[C:2]1([CH:1]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:8]#[N:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 79772-ChloropyridineHCID 8794PhenylacetonitrileHCID 24533Sodium amide

Product 1

HCID 95510alpha-Phenyl-2-pyridineacetonitrileYield 41%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a solution of benzyl cyanide (5.00 g, 42.7 mmol) and 2-chloropyridine (4.85 g, 42.7 mmol) in 15 ml of toluene was added finely powdered sodium amide (3.33 g, 85.4 mmol) in portions keeping the temperature between 20-30° C. The suspension was refluxed for 6 h. After cooling, 100 ml water is added and the product is worked up with ethyl acetate/water. After drying (MgSO4) and concentration, the crude material is purified by flash chromatography on silicagel using a 1:4 mixture of ethyl acetate and hexane as eluant to yield 3.40 g (17.5 mmol, 41%) of (RS)-phenyl-pyridin-2-yl-acetonitrile as a white solid, m.p. 89° C. and MS: m/e=194 (M+).

Workup

  1. custombetween 20-30° C
  2. temperatureThe suspension was refluxed for 6 h
  3. temperatureAfter cooling
  4. customAfter drying
  5. concentration(MgSO4) and concentration
  6. customthe crude material is purified by flash chromatography on silicagel
  7. additiona 1:4 mixture of ethyl acetate and hexane as eluant

Sources & evidence

ORD record
ord-f42a7d0885914fa18469283e5db4f2ca
Source dataset
uspto-grants-2003_04
Patent number
US06548522B1

Reaction notes

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