2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 15572903, compound

HRID 1154959Notes

Reaction equation

HRID 1154959 reaction equation
[CH3:1][N:2]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH3:27])[C:3]([CH2:5][CH:6]([CH3:20])[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]2)=[O:4].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[CH3:1][N:2]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH3:27])[C:3]([CH2:5][CH:6]([CH3:20])[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH:13]=[CH:12]2)=[O:4]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 20563547HCID 20563547, compound

Product 1

HCID 15572903HCID 15572903, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.3 g of 6-{3-[N-methyl-N-(2-methylcyclohexyl)-aminocarbonyl]-2-methylpropoxy}-3,4-dihydrocarbostyril and 3.4 g of 90% DDQ are added to 100 ml of dioxane and this mixture is refluxed for 9.5 hours and then cooled. After the reaction, the solvent is distilled off and the obtained residue is dissolved in chloroform and the organic layer is washed with aqueous saturated NaHCO3 solution, and with water, dried with anhydrous Na2SO4 and then treated with an active charcoal treatment. After distilling off the solvent, the resultant residue is refined by silica gel column chromatography (silica gel: Wakogel C-200; eluent: 10:1 chloroform-methanol (V/V)) and the crude crystals are recrystallized from benzene-ligron to produce 1.2 g of 6-{3-[N-methyl-N-(2-methylcyclohexyl)aminocarbonyl]-2-methylpropoxy}carbostyril in the form of colorless needle-like crystals. Melting point: 146°-149° C.

Workup

  1. temperaturethis mixture is refluxed for 9.5 hours
  2. temperaturecooled
  3. customAfter the reaction
  4. distillationthe solvent is distilled off
  5. dissolutionthe obtained residue is dissolved in chloroform
  6. washthe organic layer is washed with aqueous saturated NaHCO3 solution
  7. dry with materialwith water, dried with anhydrous Na2SO4
  8. additiontreated with an active charcoal treatment
  9. distillationAfter distilling off the solvent
  10. customthe crude crystals are recrystallized from benzene-ligron

Sources & evidence

ORD record
ord-47a09585c2444f6fa14b2710e2213b7d
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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