8-Hydroxyquinoline → 8-Hydroxyquinoline N-oxide

HRID 1518612Notes

Reaction equation

HRID 1518612 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:20])C=1>ClCCl>[OH:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N+:1]([O-:20])=[CH:2][CH:3]=[CH:4]2

Participants

4

Reactant 2

HCID 19238-HydroxyquinolineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 143128-Hydroxyquinoline N-oxideYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Quinolinol (351 g, 2.42 mol) was dissolved in dichloromethane (3.5 L) and, under ice-water cooling, meta-chloroperbenzoic acid (675.3 g, 2.74 mol) was added thereto in portions, and the mixture was stirred at room temperature for 2 hours. Insoluble matter was removed by filtration and was washed with dichloromethane. The filtrate and the washing were mixed and concentrated under reduced pressure. To the residue, 2% aqueous ammonia (2.1 L) was added and the mixture was stirred at room temperature overnight. The precipitate was collected by filtration, washed with purified water, and dried under reduced pressure to obtain 8-hydroxyquinoline-N-oxide (318.4 g).

Workup

  1. customInsoluble matter was removed by filtration
  2. washwas washed with dichloromethane
  3. additionThe filtrate and the washing were mixed
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue, 2% aqueous ammonia (2.1 L) was added
  6. stirringthe mixture was stirred at room temperature overnight
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with purified water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-5a798cbce38d471eb24362d5ff36d87d
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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