Reacción #1605794

ord-5a798cbce38d471eb24362d5ff36d87d

Ecuación de reacción

Oc1cccc2cccnc12
8-Quinolinol
O=C(OO)c1cccc(Cl)c1
meta-chloroperbenzoic acid
[O-][n+]1cccc2cccc(O)c21
8-hydroxyquinoline-N-oxide
Rendimiento 81.6%

Reactivos

Ninguno

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroInsoluble matter was removed by filtration
  2. 2
    Lavadowas washed with dichloromethane
  3. 3
    workup.ADDITIONThe filtrate and the washing were mixed
  4. 4
    Concentraciónconcentrated under reduced pressure
  5. 5
    workup.ADDITIONTo the residue, 2% aqueous ammonia (2.1 L) was added
  6. 6
    workup.STIRRINGthe mixture was stirred at room temperature overnight
  7. 7
    FiltraciónThe precipitate was collected by filtration
  8. 8
    Lavadowashed with purified water
  9. 9
    Otrodried under reduced pressure

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09072734B2uspto-grants-2015_07