Phenylacetonitrile → beta-Oxo-alpha-phenyl-3-pyridinepropanenitrile

HRID 2304596Notes

Reaction equation

HRID 2304596 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:12]1([CH2:18][C:19]#[N:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C.O>[C:19]([CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9])#[N:20]

Participants

6

Reactant 3

HCID 8794PhenylacetonitrileHCID 69188Ethyl NicotinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 3765543beta-Oxo-alpha-phenyl-3-pyridinepropanenitrileYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl nicotinate (10 g) and phenylacetonitrile (5.1 g) in tert-butyl alcohol (30 mL), was added potassium tert-butoxide (6.4 g), and the mixture was stirred at 100° C. for 3 h. After cooling, the resulting mixture was dissolved in water and washed with isopropyl ether. The aqueous phase was adjusted to pH 7.0 with 2 N hydrochloric acid and extracted with ethyl acetate. The extracts were washed with water, dried, and the solvent was evaporated. The crystalline residue was recrystallized from ethyl acetate-isopropyl ether to obtain the title compound (6.0 g, yield 62%).

Workup

  1. temperatureAfter cooling
  2. washwashed with isopropyl ether
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water
  5. customdried
  6. customthe solvent was evaporated
  7. customThe crystalline residue was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-63c9084de8f4468eb43b680451c5aa46
Source dataset
uspto-grants-2002_08
Patent number
US06436966B1

Reaction notes

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