Cyanoacetamide → (E,E)-2-Aminocarbonyl-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile

HRID 392480Notes

Reaction equation

HRID 392480 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]([NH2:21])=[O:20])#[N:17]>>[NH2:21][C:19](/[C:18](=[CH:8]/[CH:7]=[CH:6]/[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]([OH:13])=[C:11]([O:14][CH3:15])[CH:10]=1)/[C:16]#[N:17])=[O:20]

Participants

3

Reactant 2

HCID 7898CyanoacetamideHCID 1192162-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-

Product 1

HCID 9878647(E,E)-2-Aminocarbonyl-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile

Procedure

The compound was prepared as described in Example 3 by adding 3,5-dimethoxy-4-hydroxycinnamaldehyde (0.1 g, 0.48 mmol) to 2-cyanoacetamide (0.04 g, 0.48 mmol). After refluxing for 3 h and recrystallization from ethanol an orange solid was obtained (0.083 g, 63%). The product gave the following analytical data:

Workup

  1. customThe compound was prepared
  2. temperatureAfter refluxing for 3 h
  3. customrecrystallization from ethanol an orange solid
  4. customwas obtained (0.083 g, 63%)
  5. customThe product gave the following analytical data

Sources & evidence

ORD record
ord-0309f21459e84382866f05c2d69fe31f
Source dataset
uspto-grants-2004_10
Patent number
US06800659B2

Reaction notes

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