Reaktion #1605795

ord-5716d326ab464fea9688467c459fe100

Reaktionsgleichung

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
Ausbeute 87.4%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe insoluble matter was removed by filtration
  2. 2
    Waschenwashed with N,N-dimethylformamide
  3. 3
    workup.ADDITIONThe filtrate and the washing were mixed
  4. 4
    Einengenconcentrated under reduced pressure
  5. 5
    workup.ADDITIONTo the residue was added
  6. 6
    Sonstigepurified 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
    Waschenwashed with purified water
  10. 10
    Sonstigedried under vacuum

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09072734B2uspto-grants-2015_07