Veratraldehyde → 2-(2-Pyridyl)-3-(3,4-dimethoxy-phenyl)-2-propenenitrile

HRID 1489153

Reaction equation

HRID 1489153 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]#[N:21]>C(O)C.N1CCCCC1>[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[CH:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:20]#[N:21]

Participants

5

Reactant 2

HCID 8419VeratraldehydeHCID 75959Pyridine-2-acetonitrile

Product 1

HCID 3777302-(2-Pyridyl)-3-(3,4-dimethoxy-phenyl)-2-propenenitrile

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 2.0 g (12.0 mmole) 3,4-dimethoxybenzaldehyde in 75 ml absolute ethanol are added 1.56 g (13.3 mmole) 2-pyridylacetonitrile and 12 drops piperidine. The reaction flask is equipped with a condenser and a drying tube (using anhydrous CaSO4), and the reaction is stirred and heated. After refluxing for 6 hours, the reaction is allowed to cool to room temperature and stirred overnight for 16 hours. The solvent is removed by rotary evaporation, and the residue purified by flash chromatography on silica gel, eluting with hexane-ethyl acetate, 4:1. The yellow solid is recrystallized from acetone-hexane to give 2-(2-pyridyl)-3-(3,4-dimethoxy-phenyl)-2-propenenitrile, m.p. 112°-114° C.

Workup

  1. temperatureheated
  2. temperatureAfter refluxing for 6 hours
  3. stirringstirred overnight for 16 hours
  4. customThe solvent is removed by rotary evaporation
  5. customthe residue purified by flash chromatography on silica gel
  6. washeluting with hexane-ethyl acetate, 4:1
  7. customThe yellow solid is recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-8f6a3780991b4f058da01d1fc1c29c05
Source dataset
uspto-grants-1997_10
Patent number
US05677329

Linked notes

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