3-Phenylprop-2-Enal → HCID 12261753, compound

HRID 1904687Notes

Reaction equation

HRID 1904687 reaction equation
[CH:1](=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][NH:12][NH2:13]>C(O)C>[CH3:11][N:12]1[CH:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:2][CH:1]=[N:13]1

Participants

4

Reactant 2

HCID 3073-Phenylprop-2-EnalHCID 6061Methylhydrazine

Product 1

HCID 12261753HCID 12261753, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cinnamaldehyde (13.2 g) was added dropwise to a solution of 5 g methylhydrazine in 50 ml ethanol, and the mixture was heated under reflux for six hours. At the end of reaction, the solvent was distilled off under reduced pressure, and the residue was dissolved in 50 ml ether. The solution was washed with water and concentrated, and the concentrate was distilled under reduced pressure, giving 3.6 g (yield: 22%) of pure product. B.p.: 95°-105° C./5 mmHg; NMR (CDCl3): 2.2-3.3 (2H, m), 2.65 (3H, s), 3.76 (1H, dd, J=10, 14 Hz), 6.51 (1H, t, J=2 Hz), 7.1-7.6 (5H, m).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for six hours
  3. customAt the end of reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionthe residue was dissolved in 50 ml ether
  6. washThe solution was washed with water
  7. concentrationconcentrated
  8. distillationthe concentrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-bd384f7a641f419d84b13629d0ab2748
Source dataset
uspto-grants-1989_06
Patent number
US04839376

Reaction notes

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