2-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)- → (E,E)-2-(Phenylpropylaminocarbonyl)-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile

HRID 392478Notes

Reaction equation

HRID 392478 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:14][CH3:15])[C:12]=1[OH:13])[CH:6]=[CH:7][CH:8]=O.[C:16]([CH2:18][C:19]([N-:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:20])#[N:17]>>[C:25]1([CH2:24][CH2:23][CH2:22][NH:21][C:19](/[C:18](=[CH:8]/[CH:7]=[CH:6]/[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:12]([OH:13])=[C:11]([O:14][CH3:15])[CH:10]=2)/[C:16]#[N:17])=[O:20])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 1192162-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-HCID 178511183HCID 178511183, compound

Product 1

HCID 10157333(E,E)-2-(Phenylpropylaminocarbonyl)-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrileYield 90.2%

Procedure

The compound was prepared as described in Example 3 by adding 3,5-dimethoxy-4 hydroxycinnamaldehyde (0.10 g, 0.48 mmol) to N-(cyanoacetyl)phenylpropylamide (Example 19, 0.097 g, 0.48 mmol). After refluxing for 3 h the residue was purified by silica gel chromatography (CHCl3-hexane, 1:1) to give a brown solid (0.17 g, 90% yield). The product gave the following analytical data:

Workup

  1. customThe compound was prepared
  2. temperatureAfter refluxing for 3 h the residue
  3. customwas purified by silica gel chromatography (CHCl3-hexane, 1:1)

Sources & evidence

ORD record
ord-4f4e0d95ecd14b58a1b3605306955404
Source dataset
uspto-grants-2004_10
Patent number
US06800659B2

Reaction notes

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