Reaktion #1605798

Reaktionsgleichung

8-Benzyloxy-5-((R)-2-bromo-1-hyroxyethyl)-1H-quinolin-2-one

sodium azide

Sodium azide

→

5-((R)-2-azido-1-hyroxyethyl)-8-benzyloxy-1H-quinolin-2-one

Ausbeute 90.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at the same temperature overnight
2. 2
   workup.ADDITIONTo the reaction solution was added
3. 3
   Sonstigepurified water
4. 4
   workup.STIRRINGstirred at room temperature for 1 hour
5. 5
   FiltrationThe precipitate was collected by filtration
6. 6
   Waschenwashed with purified water
7. 7
   SonstigeBy drying under reduced pressure

Vorschrift

8-Benzyloxy-5-((R)-2-bromo-1-hyroxyethyl)-1H-quinolin-2-one (20.8 g, 55.6 mmol) and sodium azide (3.61 g, 55.5 mmol) were suspended in N,N-dimethylformamide (100 mL) and the mixture was stirred at 65° C. for 3 hours. Sodium azide (1.81 g, 27.8 mmol) was added thereto and the mixture was stirred at the same temperature overnight. To the reaction solution was added purified water and stirred at room temperature for 1 hour. The precipitate was collected by filtration and washed with purified water. By drying under reduced pressure, 5-((R)-2-azido-1-hyroxyethyl)-8-benzyloxy-1H-quinolin-2-one (16.8 g) was obtained.

Quelle