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

HRID 926993
Notes
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Reaction equation

HRID 926993 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

HCID 1178995645,6,7,8-Tetrahydroquinolin-5-one N-oxideYield 83.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3520671ade864827b17cbe7923004bab
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290440B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes