Potassium Carbonate → 3-(4-Fluorophenyl)-3-oxo-2-(4-pyridinyl)propanenitrile

HRID 1635922Notes

Reaction equation

HRID 1635922 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]#[N:9])=[CH:3][CH:2]=1.[F:10][C:11]1[CH:26]=[CH:25][C:14]([C:15](ON2C(=O)CCC2=O)=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:10][C:11]1[CH:26]=[CH:25][C:14]([C:15](=[O:16])[CH:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[C:8]#[N:9])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41120852-(Pyridin-4-yl)acetonitrileHCID 100143742,5-Dioxopyrrolidin-1-yl 4-fluorobenzoate

Product 1

HCID 186256553-(4-Fluorophenyl)-3-oxo-2-(4-pyridinyl)propanenitrileYield 103%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

32 g of 4-pyridylacetonitrile and 86 g of 2,5-dioxo-pyrrolidinyl 4-fluorobenzoate were dissolved in 1.3 L of dimethylformamide. After the addition of 164 g of potassium carbonate, the resulting mixture was stirred at room temperature for a day. After the reaction mixture was filtered through cerite, the filtrate was concentrated under reduced pressure. After water was added to the residue, this solution was neutralized with an aqueous solution of hydrochloric acid. The precipitated crystals were collected by filtration, washed with diethyl ether, and then dried in a stream of air to obtain 67 g (103% yield) of the title compound.

Workup

  1. filtrationAfter the reaction mixture was filtered through cerite, the filtrate
  2. concentrationwas concentrated under reduced pressure
  3. additionAfter water was added to the residue
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with diethyl ether
  6. customdried in a stream of air

Sources & evidence

ORD record
ord-afd8a8dae8974d04a906caaa3f1f12c8
Source dataset
uspto-grants-2003_01
Patent number
US06511997B1

Reaction notes

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