Reaktion #1605796

Reaktionsgleichung

5-Acetyl-8-benzyloxy-1H-quinolin-2-one

Pyridinium tribromide

→

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one

Ausbeute 81.9%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturin portions, and the mixture was heated
2. 2
   Temperaturunder reflux for 3 hours
3. 3
   Temperaturthe mixture was heated
4. 4
   Temperaturunder reflux overnight
5. 5
   FiltrationThe precipitate was collected by filtration
6. 6
   Waschenwashed with tetrahydrofuran
7. 7
   WaschenThe solid was suspension-washed with tetrahydrofuran (2.3 L)
8. 8
   Waschenwashed with purified water (3 L)
9. 9
   workup.ADDITIONSeparately, the tetrahydrofuran filtrate and the washings were mixed
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    Waschenthe residue was suspension-washed with tetrahydrofuran (1 L)
12. 12
    Sonstigedried under reduced pressure

Vorschrift

5-Acetyl-8-benzyloxy-1H-quinolin-2-one (372 g, 1.27 mol) was dissolved in tetrahydrofuran (3.6 L) and the solution was cooled to 0° C. Pyridinium tribromide (453 g, 1.27 mol) was added thereto in portions, and the mixture was heated under reflux for 3 hours. Thereafter, tetrahydrofuran (3.1 L) was added and the mixture was heated under reflux overnight. The precipitate was collected by filtration and washed with tetrahydrofuran. The solid was suspension-washed with tetrahydrofuran (2.3 L) and, thereafter, washed with purified water (3 L). Separately, the tetrahydrofuran filtrate and the washings were mixed, concentrated under reduced pressure, and the residue was suspension-washed with tetrahydrofuran (1 L). The solids were combined and dried under reduced pressure to obtain 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one (387 g).

Quelle