2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-(N-acetyl-N-methylamino)-12-methylene-5,6,7,12-tetrahydrodibenzo[a,d]cyclooctene

HRID 1758727

Reaction equation

HRID 1758727 reaction equation
[C:1]([N:4]([CH:6]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]([CH3:18])[C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]=2[CH2:8][CH2:7]1)[CH3:5])(=[O:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[C:1]([N:4]([CH:6]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=[CH2:18])[C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]=2[CH2:8][CH2:7]1)[CH3:5])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 125337635-(N-Acetyl-N-methylamino)-12-methyl-5,6,7,12-tetrahydrodibenzo[a,d]cyclooctene

Product 1

HCID 125337645-(N-acetyl-N-methylamino)-12-methylene-5,6,7,12-tetrahydrodibenzo[a,d]cyclooctene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-(N-Acetyl-N-methylamino)-12-methyl-5,6,7,12-tetrahydrodibenzo[a,d]cyclooctene (10.5 g., 34 mmole), dichlorodicyanobenzoquinone (9.5 g. of 98%, 41 mmole) and 750 ml. of benzene were combined and heated at reflux under nitrogen for 3.5 hours. The mixture was cooled, washed four times with 1 M sodium hydroxide solution and twice with water, dried over potassium carbonate, treated with about 0.5 g. of decolorizing carbon, filtered, and evaporated in vacuo to give 10.5 g. of brown oil.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 3.5 hours
  3. temperatureThe mixture was cooled
  4. washwashed four times with 1 M sodium hydroxide solution
  5. dry with materialtwice with water, dried over potassium carbonate
  6. additiontreated with about 0.5 g
  7. filtrationof decolorizing carbon, filtered
  8. customevaporated in vacuo
  9. customto give 10.5 g

Sources & evidence

ORD record
ord-771b750f2e7f4924a32a9345176ba027
Source dataset
uspto-grants-1983_02
Patent number
US04374838

Linked notes

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