2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178428824, compound

HRID 581776Notes

Reaction equation

HRID 581776 reaction equation
[Cl:1][C:2]1[C:32]([N+:33]([O-:35])=[O:34])=[CH:31][CH:30]=[C:29]([Cl:36])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]2[O:17]CC1C=CC(OC)=C(OC)C=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl.O>[Cl:1][C:2]1[C:32]([N+:33]([O-:35])=[O:34])=[CH:31][CH:30]=[C:29]([Cl:36])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]2[OH:17]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22113044HCID 22113044, compound

Product 1

HCID 178428824HCID 178428824, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

A mixture of 8-(2,6-dichloro-3-nitrobenzyloxy)-4-(3,4-dimethoxybenzyloxy)-2-methylquinoline (106 mg), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (50 mg) and dichloromethane-water (18:1, V/V, 2.85 ml) was heated under reflux for 19 hours. The reaction mixture was partitioned into dichloromethane and saturated aqueous sodium hydrogen carbonate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a preparative thin-layer chromatography (dichloromethane-methanol) followed by washing with ethanol to give a brownish powder (26 mg) of 8-(2,6-dichloro-3-nitrobenzyloxy)-4-hydroxy-2-methylquinoline. mp: 255-258° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 19 hours
  3. customThe reaction mixture was partitioned into dichloromethane and saturated aqueous sodium hydrogen carbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by a preparative thin-layer chromatography (dichloromethane-methanol)
  8. washby washing with ethanol

Sources & evidence

ORD record
ord-de7d94a122ff4d72884688e8a3b8b3b2
Source dataset
uspto-grants-1999_07
Patent number
US05922711

Reaction notes

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