Réaction #1605795

ord-5716d326ab464fea9688467c459fe100

Équation de réaction

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
Rendement 87.4%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09072734B2uspto-grants-2015_07