m-Chloroperbenzoic acid → 5,6,7,8-Tetrahydroquinolin-5-one N-oxide

HRID 926993

Reaktionsgleichung

Reaktionsgleichung von HRID 926993
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:20])C=1.C(=O)([O-])O.[Na+]>ClCCl.C(Cl)(Cl)Cl>[N+:1]1([O-:20])[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 30168115(6H)-Quinolinone, 7,8-dihydro-

Produkt 1

HCID 1178995645,6,7,8-Tetrahydroquinolin-5-one N-oxideAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5,6,7,8-Tetrahydroquinolin-5-one (7.12 g) was dissolved in dichloromethane (138 mL), added with 3-chloroperbenzoic acid (14.5 g) under ice cooling, and stirred for 4 hours at the same temperature. After adding a saturated aqueous solution of sodium hydrogen carbonate and diluting with chloroform, insoluble was removed by filtration through Celite. After adding 1 mol/L aqueous solution of sodium hydroxide, it was extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure. The residues were suspended in diethyl ether and collected by filtration to obtain the title compound (6.61 g) as a yellow powder.

Aufarbeitung

  1. custominsoluble was removed by filtration through Celite
  2. additionAfter adding 1 mol/L aqueous solution of sodium hydroxide, it
  3. extractionwas extracted with chloroform
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was then evaporated under reduced pressure
  6. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-3520671ade864827b17cbe7923004bab
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290440B2

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