Reacción #1605798

Ecuación de reacción

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

Rendimiento 90.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente