3-(4-Nitrophenyl)prop-2-enal → (E,E)-2-(3,4-Dihydroxybenzylaminocarbonyl)-3-(4-nitrostyryl)acrylonitrile

HRID 392483Notes

Reaction equation

HRID 392483 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][CH:10]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14]([CH2:16][C:17]([N-:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([OH:28])[CH:22]=1)=[O:18])#[N:15]>>[OH:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[OH:27])[CH2:20][NH:19][C:17](/[C:16](=[CH:10]/[CH:9]=[CH:8]/[C:7]1[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)/[C:14]#[N:15])=[O:18]

Participants

3

Reactant 2

HCID 156143-(4-Nitrophenyl)prop-2-enalHCID 178511180HCID 178511180, compound

Product 1

HCID 9947247(E,E)-2-(3,4-Dihydroxybenzylaminocarbonyl)-3-(4-nitrostyryl)acrylonitrile

Procedure

The compound was prepared as described in Example 3 by adding 4-nitrocinnamaldehyde (0.009 g, 0.05 mmol) to N-(cyanoacetyl)3,4-dihydroxybenzylamide (Example 2, 0.010 g, 0.05 mmol). After refluxing for 2 h and recrystallization from ethanol a yellow solid was obtained (0.007 g, 39%). The product gave the following analytical data:

Workup

  1. customThe compound was prepared
  2. temperatureAfter refluxing for 2 h
  3. customrecrystallization from ethanol a yellow solid
  4. customwas obtained (0.007 g, 39%)
  5. customThe product gave the following analytical data

Sources & evidence

ORD record
ord-db425cebb19a4301a6647668f8c97cf4
Source dataset
uspto-grants-2004_10
Patent number
US06800659B2

Reaction notes

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