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

HRID 1489155Notes

Reaction equation

HRID 1489155 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.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23]#[N:24])=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22](=[CH:6][C:5]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:23]#[N:24])=[CH:14]1

Participants

5

Reactant 3

HCID 8419VeratraldehydeHCID 11430Potassium CarbonateHCID 351795Indole-3-acetonitrile

Product 1

HCID 543456942-(3-Indolyl)-3-(3,4-dimethoxy-phenyl)-2-propenenitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2.0 g (12.0 mmole) 3,4-dimethoxybenzaldehyde in 75 ml absolute ethanol are added 2.07 g (13.3 mmole) 3-indolylacetonitrile and 1.83 g (13.3 mmole) anhydrous potassium carbonate. The reaction flask is equipped with a condenser and a drying tube (using anhydrous CaSO4), and the reaction was stirred and heated. After refluxing for 24 hours, the reaction is allowed to cool to room temperature. The reaction mixture is filtered to remove the salts, and the solvent is removed by rotary evaporation. The residue is purified by flash chromatography on silica gel, eluting with hexane-ethyl acetate, 3:1. The yellow solid is recrystallized from acetone-hexane to give 2-(3-indolyl)-3-(3,4-dimethoxy-phenyl)-2-propenenitrile, m.p. 139°-141° C.

Workup

  1. temperatureheated
  2. temperatureAfter refluxing for 24 hours
  3. filtrationThe reaction mixture is filtered
  4. customto remove the salts
  5. customthe solvent is removed by rotary evaporation
  6. customThe residue is purified by flash chromatography on silica gel
  7. washeluting with hexane-ethyl acetate, 3:1
  8. customThe yellow solid is recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-043a06b63eac4890866b1db87b1fdc1e
Source dataset
uspto-grants-1997_10
Patent number
US05677329

Reaction notes

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