Réaction #1605796

Équation de réaction

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

Pyridinium tribromide

→

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

Rendement 81.9%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurein portions, and the mixture was heated
2. 2
   Températureunder reflux for 3 hours
3. 3
   Températurethe mixture was heated
4. 4
   Températureunder reflux overnight
5. 5
   FiltrationThe precipitate was collected by filtration
6. 6
   Lavagewashed with tetrahydrofuran
7. 7
   LavageThe solid was suspension-washed with tetrahydrofuran (2.3 L)
8. 8
   Lavagewashed with purified water (3 L)
9. 9
   workup.ADDITIONSeparately, the tetrahydrofuran filtrate and the washings were mixed
10. 10
    Concentrationconcentrated under reduced pressure
11. 11
    Lavagethe residue was suspension-washed with tetrahydrofuran (1 L)
12. 12
    Autredried under reduced pressure

Mode opératoire

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).

Source