تفاعل #1605796

معادلة التفاعل

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

Pyridinium tribromide

→

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

المردود 81.9%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةin portions, and the mixture was heated
2. 2
   درجة الحرارةunder reflux for 3 hours
3. 3
   درجة الحرارةthe mixture was heated
4. 4
   درجة الحرارةunder reflux overnight
5. 5
   ترشيحThe precipitate was collected by filtration
6. 6
   غسيلwashed with tetrahydrofuran
7. 7
   غسيلThe solid was suspension-washed with tetrahydrofuran (2.3 L)
8. 8
   غسيلwashed with purified water (3 L)
9. 9
   workup.ADDITIONSeparately, the tetrahydrofuran filtrate and the washings were mixed
10. 10
    تركيزconcentrated under reduced pressure
11. 11
    غسيلthe residue was suspension-washed with tetrahydrofuran (1 L)
12. 12
    أخرىdried under reduced pressure

الإجراء التجريبي

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).

المصدر