Reaktion #1605821

ord-72683aafa728470ea560b7a837fa0a00

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
COc1ccc(CCl)cc1
4-methoxybenzyl chloride
COc1ccc(COc2ccc(C(C)=O)c3ccc(=O)[nH]c23)cc1
5-acetyl-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one
Ausbeute 53.8%

Lösungsmittel

Reaktionsbedingungen

Temperatur
90°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONTo the reaction mixture was added
  2. 2
    Sonstigepurified water (0.5 L)
  3. 3
    workup.STIRRINGthe mixture was stirred at room temperature overnight
  4. 4
    FiltrationThe precipitate was collected by filtration
  5. 5
    Waschenwashed with purified water
  6. 6
    Sonstigedried under reduced pressure

Vorschrift

5-Acetyl-8-hydroxy-1H-quinolin-2-one (29.5 g, 0.15 mol) was suspended in N,N-dimethylformamide (145 mL), potassium carbonate (22.2 g, 0.16 mol) and successively 4-methoxybenzyl chloride (22.7 g, 0.15 mol) were added thereto, and the mixture was stirred at 90° C. overnight. To the reaction mixture was added purified water (0.5 L) and the mixture was stirred at room temperature overnight. The precipitate was collected by filtration, washed with purified water, dried under reduced pressure to obtain 5-acetyl-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (26.1 g).

Quelle

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