3-Pyridinecarboxaldehyde → 3-(3-Pyridinyl)-2-propenenitrile

HRID 1594646Notes

Reaction equation

HRID 1594646 reaction equation
C(OP([CH2:9][C:10]#[N:11])(=O)OCC)C.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=O)[CH:13]=1>C1(C)C=CC=CC=1>[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=[CH:9][C:10]#[N:11])[CH:13]=1

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 537301363-(3-Pyridinyl)-2-propenenitrileYield 69.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

95 ml (0.60 mol) of cyanomethylphosphonic acid diethyl ester and 50 ml (0.55 mol) of pyridine-3-carbaldehyde are dissolved in 1 L of toluene and mixed with 55 g (0.55 mol) of KHCO3. The mixture is heated for 1 hour in a preheated oil bath. The cooled mixture is mixed with additional toluene and washed with 1M NaHCO3, twice with water and with saturated common salt solution. The organic phase is dried and concentrated by evaporation in a vacuum. The residue is recrystallized from ethyl acetate/hexane, and 49.5 g (69%) of product is obtained. Melting point 99.5-101° C.

Workup

  1. temperatureThe mixture is heated for 1 hour in a preheated oil bath
  2. washwashed with 1M NaHCO3, twice with water and with saturated common salt solution
  3. customThe organic phase is dried
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-9b32bfbfa3d54b59838abd9c04d7dd00
Source dataset
uspto-grants-2001_09
Patent number
US06284779B1

Reaction notes

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