Реакция #1605796

Уравнение реакции

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

Pyridinium tribromide

→

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

Выход 81.9%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураin portions, and the mixture was heated
2. 2
   Температураunder reflux for 3 hours
3. 3
   Температураthe mixture was heated
4. 4
   Температураunder reflux overnight
5. 5
   ФильтрацияThe precipitate was collected by filtration
6. 6
   Промывкаwashed with tetrahydrofuran
7. 7
   ПромывкаThe solid was suspension-washed with tetrahydrofuran (2.3 L)
8. 8
   Промывкаwashed with purified water (3 L)
9. 9
   workup.ADDITIONSeparately, the tetrahydrofuran filtrate and the washings were mixed
10. 10
    Концентрированиеconcentrated under reduced pressure
11. 11
    Промывкаthe residue was suspension-washed with tetrahydrofuran (1 L)
12. 12
    Другоеdried under reduced pressure

Методика

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).

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