Reacción #1605796

Ecuación de reacción

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

Pyridinium tribromide

→

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

Rendimiento 81.9%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturain portions, and the mixture was heated
2. 2
   Temperaturaunder reflux for 3 hours
3. 3
   Temperaturathe mixture was heated
4. 4
   Temperaturaunder reflux overnight
5. 5
   FiltraciónThe precipitate was collected by filtration
6. 6
   Lavadowashed with tetrahydrofuran
7. 7
   LavadoThe solid was suspension-washed with tetrahydrofuran (2.3 L)
8. 8
   Lavadowashed with purified water (3 L)
9. 9
   workup.ADDITIONSeparately, the tetrahydrofuran filtrate and the washings were mixed
10. 10
    Concentraciónconcentrated under reduced pressure
11. 11
    Lavadothe residue was suspension-washed with tetrahydrofuran (1 L)
12. 12
    Otrodried under reduced pressure

Procedimiento

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).

Fuente