Malononitrile → [(3,4-Dimethoxyphenyl)methylidene]propanedinitrile

HRID 1647711Notes

Reaction equation

HRID 1647711 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH:11]=O>C(O)C>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH:11]=[C:2]([C:1]#[N:5])[C:3]#[N:4]

Participants

4

Reactant 2

HCID 8010MalononitrileHCID 8419Veratraldehyde

Product 1

HCID 219691[(3,4-Dimethoxyphenyl)methylidene]propanedinitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of malononitrile (7.52 g) and 3,4-dimethoxybenzaldehyde (18.95 g) in ethanol (100 ml) was warmed to reflux temperature with stirring. The orange solution was removed from the heat and piperidine (0.5 ml) added down the condenser. Once the vigorous reaction had subsided, the reaction mixture was reheated to reflux temperature and this maintained for 35 minutes. Copious quantities of a bright yellow solid had appeared by this time. The mixture was cooled in an ice bath for 10 minutes and the yellow solid filtered off, washed with ethanol and ether and dried in vacuo at 70° C. yielding 3,4-dimethoxy benzylidenemalononitrile, m.p.137° C.

Workup

  1. temperaturewas warmed
  2. temperatureto reflux temperature
  3. customThe orange solution was removed from the
  4. temperatureheat
  5. additionpiperidine (0.5 ml) added down the condenser
  6. customOnce the vigorous reaction
  7. temperatureto reflux temperature
  8. temperaturethis maintained for 35 minutes
  9. temperatureThe mixture was cooled in an ice bath for 10 minutes
  10. filtrationthe yellow solid filtered off
  11. washwashed with ethanol and ether
  12. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-4cc6771484df47dc80093b8380cc0ce4
Source dataset
uspto-grants-1995_07
Patent number
US05434160

Reaction notes

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