2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178516364, compound

HRID 650529Notes

Reaction equation

HRID 650529 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=2)[C:4](=[O:15])[CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=2)[C:4]([OH:15])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 6075412,3-Dihydrobenzo[g]quinolin-4(1H)-one

Product 1

HCID 178516364HCID 178516364, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 1 g of 2,3-Dihydrobenzo[g]quinolin-4(1H)-one (5) (5.07 mmol) in 20 mL of toluene (0.25 M) under a nitrogen atmosphere was added 1.5 g of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ, 1.3 equivalents). The reaction mixture was heated to reflux and monitored by TLC until completion (approximately 2 h). After cooling to rt, the mixture was concentrated in vacuo then filtered through a silica plug using 10% methanol in methylene chloride to afford crude phenol (6). Subsequently, the crude phenol was directly subjected to the halogenation conditions of step 2.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. custommonitored by TLC until completion (approximately 2 h)
  4. concentrationthe mixture was concentrated in vacuo
  5. filtrationthen filtered through a silica plug

Sources & evidence

ORD record
ord-74bffb8afded47258c256695086c20de
Source dataset
uspto-grants-2001_08
Patent number
US06274596B1

Reaction notes

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