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

HRID 1277422노트

반응식

HRID 1277422 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8b1955972c244624baf6b2bf57905678
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04277479

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