3-Methoxy-4-hydroxy-5-nitrocinnamaldehyde → (E,E)-2-(3,4-Dihydroxybenzylaminocarbonyl)-3-(3-methoxy-4-hydroxy-5-nitrostyryl)acrylonitrile

HRID 1818049Notes

Reaction equation

HRID 1818049 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[C:12]=1[OH:13])[CH:6]=[CH:7][CH:8]=O.[C:17]([CH2:19][C:20]([N-:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([OH:31])[CH:25]=1)=[O:21])#[N:18]>>[OH:31][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[OH:30])[CH2:23][NH:22][C:20](/[C:19](=[CH:8]/[CH:7]=[CH:6]/[C:5]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[C:12]([OH:13])=[C:3]([O:2][CH3:1])[CH:4]=1)/[C:17]#[N:18])=[O:21]

Participants

3

Reactant 2

HCID 734125653-Methoxy-4-hydroxy-5-nitrocinnamaldehydeHCID 178511180HCID 178511180, compound

Product 1

HCID 11538812(E,E)-2-(3,4-Dihydroxybenzylaminocarbonyl)-3-(3-methoxy-4-hydroxy-5-nitrostyryl)acrylonitrile

Procedure

The compound was prepared as described in Example 3 by adding 3-methoxy-4-hydroxy-5-nitrocinnamaldehyde (22 mg, 0.1 mmol) to N-(cyanoacetyl)3,4-dihydroxybenzylamide (21 mg, 0.1 mmol). After refluxing for 4 h and recrystallization from ethanol-water an orange solid was obtained (19 mg, 46%). The product gave the following analytical data:

Workup

  1. customThe compound was prepared
  2. temperatureAfter refluxing for 4 h
  3. customrecrystallization from ethanol-water an orange solid
  4. customwas obtained (19 mg, 46%)
  5. customThe product gave the following analytical data

Sources & evidence

ORD record
ord-bc58f77f663d4fb7b859da4960e22077
Source dataset
uspto-grants-2009_10
Patent number
US07598419B2

Reaction notes

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