3-Fluorobenzaldehyde → (E)-3-(3-Fluorophenyl)-2-(4-pyridyl)-2-propenenitrile

HRID 1373006Notes

Reaction equation

HRID 1373006 reaction equation
[Na].Cl.[N:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O>C(O)C>[F:12][C:13]1[CH:14]=[C:15](/[CH:16]=[C:9](\[C:6]2[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=2)/[C:10]#[N:11])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 680093-FluorobenzaldehydeHCID 5360545SodiumHCID 123966084-Pyridylacetonitrile hydrochloride

Product 1

HCID 57435651(E)-3-(3-Fluorophenyl)-2-(4-pyridyl)-2-propenenitrileYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (3.0 g, 130 mmol) was dissolved in ethanol (150 mL), 4-pyridylacetonitrile hydrochloride (10 g, 65 mmol) was added thereto, and then the mixture was stirred at room temperature. After 10 minutes, 3-fluorobenzaldehyde (8 g, 65 mmol) was added thereto, followed by stirring as it was for 30 minutes. The resulting precipitates were collected by filtration and washed with a small portion of water, to give the title compound (8.2 g, 56%) as a colorless solid.

Workup

  1. stirringby stirring as it
  2. waitwas for 30 minutes
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with a small portion of water

Sources & evidence

ORD record
ord-f8a9a4dd6931466b864635aa54c61609
Source dataset
uspto-grants-2007_01
Patent number
US07160892B2

Reaction notes

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