2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Nitrophenanthrene

HRID 68501Notes

Reaction equation

HRID 68501 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7][C:6]=2[CH:5]=1)([O-:3])=[O:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[N+:1]([C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 792362-Nitro-9,10-dihydrophenanthrene

Product 1

HCID 282062-NitrophenanthreneYield 60.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under an argon atmosphere, 225 g of 2-nitro-9,10-dihydrophenanthrene, 227 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone, and 2.4 L of 1,4-dioxane were added, and then the mixture was stirred for 24 hours under heating reflux. After having been cooled to room temperature, the reaction solution was concentrated. The residue was purified by silica gel column chromatography, and was then washed with methanol. Thus, 134 g of a white crystal were obtained (in 60% yield).

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. concentrationthe reaction solution was concentrated
  4. customThe residue was purified by silica gel column chromatography
  5. washwas then washed with methanol

Sources & evidence

ORD record
ord-0f59391e7351493fb54b705001d63d56
Source dataset
uspto-grants-2014_09
Patent number
US08822041B2

Reaction notes

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