Water → 2-(4-Fluorophenyl)-3-oxo-3-(pyridin-4-yl)propanenitrile

HRID 2260521Notes

Reaction equation

HRID 2260521 reaction equation
[Na].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[C:12](OCC)(=[O:19])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.O>C(O)C>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:10]#[N:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15291Ethyl isonicotinateHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 5360545Sodium

Product 1

HCID 141952232-(4-Fluorophenyl)-3-oxo-3-(pyridin-4-yl)propanenitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (2.48 g) was dissolved in dry ethanol (37 ml) under nitrogen atmosphere. To the solution was added 4-fluorophenylacetonitrile (11.65 g) and ethyl isonicotinate (16.41 ml) and the solution was refluxed for hours. The reaction mixture was cooled and poured into water. The ethanol of the mixture was removed under reduced pressure. The resulting aqueous solution was washed with ether and neutralized with diluted hydrochloric acid. The separated solid was collected, washed with water and dried to give 2-(4-fluorophenyl)-3-oxo-3-(pyridin-4-yl)propanenitrile (16.43 g).

Workup

  1. temperaturethe solution was refluxed for hours
  2. temperatureThe reaction mixture was cooled
  3. customThe ethanol of the mixture was removed under reduced pressure
  4. washThe resulting aqueous solution was washed with ether and neutralized with diluted hydrochloric acid
  5. customThe separated solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-8c0ab2fe191c48b4a725358d102d69a1
Source dataset
uspto-grants-1995_12
Patent number
US05478827

Reaction notes

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