2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 11096910, compound

HRID 868165Notes

Reaction equation

HRID 868165 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][NH:8][CH:7]([C:15]([O:17][CH3:18])=[O:16])[CH2:6]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[N:8][C:7]([C:15]([O:17][CH3:18])=[O:16])=[CH:6]2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 5301401Methyl 1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylate

Product 1

HCID 11096910HCID 11096910, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid, methyl ester (19.77 g, 78.7 mmol) in 400 ml of tetrahydrofuran, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (39.3 g, 173.1 mmol) was added. The dark solution was heated under reflux overnight. The resulting precipitate was filtered off, dissolved in 500 ml dichloromethane/water 1:1, and the pH was adjusted to 10 by means of 1N sodium hydroxide. The phases were separated, the aqueous phase extracted once with dichloromethane and the combined organic phases washed twice with 100 ml of water containing a few drops of 1N sodium hydroxide. After the drying and evaporating of the solvent, 9.20 g of the title compound was obtained; melting point 214.9° C.

Workup

  1. temperatureThe dark solution was heated
  2. temperatureunder reflux overnight
  3. filtrationThe resulting precipitate was filtered off
  4. dissolutiondissolved in 500 ml dichloromethane/water 1:1
  5. customThe phases were separated
  6. extractionthe aqueous phase extracted once with dichloromethane
  7. washthe combined organic phases washed twice with 100 ml of water containing a few drops of 1N sodium hydroxide
  8. customAfter the drying and evaporating of the solvent

Sources & evidence

ORD record
ord-c45f6cad1ae4439db8e86825b96d7708
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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