2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-[3-(1-Cyclohexyl-1H-tetrazol-5-yl) propoxy]-2(1H)-quinolinone

HRID 1277422Notes

Reaction equation

HRID 1277422 reaction equation
[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]4)=[N:10][N:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.O1CCOCC1>C(Cl)(Cl)Cl>[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:26])[CH:20]=[CH:19]4)=[N:10][N:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-DioxaneHCID 129412676-[3-(1-Cyclohexyl-1H-tetrazol-5-yl)propoxy]-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 130210946-[3-(1-Cyclohexyl-1H-tetrazol-5-yl) propoxy]-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.2 Grams of 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril and 3.4 g of 90% DDQ are added to 100 ml of dioxane and this mixture is refluxed for9.5 hours and then cooled. After the reaction is completed, the solvent is distilled off and the residue obtained is dissolved in chloroform and the organic layer is washed with aqueous saturated NaHCO3 solution, and with water then dried with Na2SO4 and treated with an activatedcharcoal. After the solvent is removed by distillation, the resultant residue is refined by silica gel column chromatography [silica gel: Wakogel C-200; eluent:chloroform:methanol=10:1 (V/V)] and the crude crystals are recrystallized from chloroform to obtain 1.1 g of 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]carbostyril in the form of colorless needle-like crystals. Melting point: 211°-212° C.

Workup

  1. temperaturethis mixture is refluxed for9
  2. temperature5 hours and then cooled
  3. distillationthe solvent is distilled off
  4. customthe residue obtained
  5. washthe organic layer is washed with aqueous saturated NaHCO3 solution
  6. dry with materialwith water then dried with Na2SO4
  7. additiontreated with an activatedcharcoal
  8. customAfter the solvent is removed by distillation
  9. customthe crude crystals are recrystallized from chloroform

Sources & evidence

ORD record
ord-8b1955972c244624baf6b2bf57905678
Source dataset
uspto-grants-1981_07
Patent number
US04277479

Reaction notes

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