2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 23067304, compound

HRID 428144Notes

Reaction equation

HRID 428144 reaction equation
[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=1)[CH2:3][N:4]([CH3:15])[C:5](=[O:14])/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH3:15][N:4]([CH2:3][C:2]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=1)=[O:1])[C:5](=[O:14])/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 20701426HCID 20701426, compound

Product 1

HCID 23067304HCID 23067304, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (E)-N-[2-hydroxy-2-(3-methoxy-4-hydroxyphenyl)ethyl]-N-methyl-3-(3-pyridyl)-2-propenoic acid amide (656 mg, 2 mmol) in dioxane (12 ml), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (468 mg, 2 mmol) was added under argon and stirred at room temperature for 2 hours. After the precipitated crystal was filtered out, the solvent was distilled out under reduced pressure and the residue was purified by column chromatography (chloroform:methanol=50:1) and dried under reduced pressure to yield the titled compound (362 mg, 56%).

Workup

  1. filtrationAfter the precipitated crystal was filtered out
  2. distillationthe solvent was distilled out under reduced pressure
  3. customthe residue was purified by column chromatography (chloroform:methanol=50:1)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-696849d4a53e4d069e1598c661f96d8a
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Reaction notes

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