Potassium Carbonate → 2-(3-Pyridyl)-3-(2,4-dichlorophenyl)-2-propenenitrile

HRID 36898

Reaction equation

HRID 36898 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18]#[N:19])[CH:12]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[CH:4][C:3]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=2[Cl:1])[C:18]#[N:19])[CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 134042,4-DichlorobenzaldehydeHCID 809233-Pyridineacetonitrile

Product 1

HCID 542432932-(3-Pyridyl)-3-(2,4-dichlorophenyl)-2-propenenitrileYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2,4-dichlorobenzaldehyde (5.0 g, 29 mmole) and 3-pyridylacetonitrile (3.05 ml, 29 mmole) in 150 ml absolute ethanol were added 3.95 g K2CO3. After stirring for about 15 minutes, a white solid precipitated out of the reaction mixture. The reaction mixture was stirred overnight and filtered. The filter cake was washed with absolute ethanol and dissolve in CH2Cl2. The CH2Cl2 solution was filtered and concentrated in vacuo. The resulting white solid was recrystallized from 3:2 hexane/ethyl acetate to give 6.0 g (76%) of the title compound.

Workup

  1. customa white solid precipitated out of the reaction mixture
  2. stirringThe reaction mixture was stirred overnight
  3. filtrationfiltered
  4. washThe filter cake was washed with absolute ethanol
  5. dissolutiondissolve in CH2Cl2
  6. filtrationThe CH2Cl2 solution was filtered
  7. concentrationconcentrated in vacuo
  8. customThe resulting white solid was recrystallized from 3:2 hexane/ethyl acetate

Sources & evidence

ORD record
ord-5b8a828504824dbfaf9b32d9a5bbc2d0
Source dataset
uspto-grants-1995_05
Patent number
US05418245

Linked notes

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