Reacción #1605795

ord-5716d326ab464fea9688467c459fe100

Ecuación de reacción

CC(=O)c1ccc(O)c2[nH]c(=O)ccc12
5-Acetyl-8-hydroxy-1H-quinolin-2-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate
BrCc1ccccc1
benzyl bromide
CC(=O)c1ccc(OCc2ccccc2)c2[nH]c(=O)ccc12
5-acetyl-8-benzyloxy-1H-quinolin-2-one
Rendimiento 87.4%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe insoluble matter was removed by filtration
  2. 2
    Lavadowashed with N,N-dimethylformamide
  3. 3
    workup.ADDITIONThe filtrate and the washing were mixed
  4. 4
    Concentraciónconcentrated under reduced pressure
  5. 5
    workup.ADDITIONTo the residue was added
  6. 6
    Otropurified water (3.3 L)
  7. 7
    workup.STIRRINGthe mixture was stirred at room temperature overnight
  8. 8
    FiltraciónThe precipitate was collected by filtration
  9. 9
    Lavadowashed with purified water
  10. 10
    Otrodried under vacuum

Procedimiento

5-Acetyl-8-hydroxy-1H-quinolin-2-one (430 g, 2.12 mol) was suspended in N,N-dimethylformamide (3.3 L), potassium carbonate (298 g, 2.16 mol) and subsequently benzyl bromide (298 g, 2.11 mol) were added thereto, and the mixture was stirred at room temperature for 2 hours. The insoluble matter was removed by filtration and washed with N,N-dimethylformamide. The filtrate and the washing were mixed and concentrated under reduced pressure. To the residue was added purified water (3.3 L) and the mixture was stirred at room temperature overnight. The precipitate was collected by filtration, washed with purified water, and dried under vacuum to obtain 5-acetyl-8-benzyloxy-1H-quinolin-2-one (541 g).

Fuente

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