Reacción #68012

Ecuación de reacción

8-methylquinolin-2(1H)-one

sodium hydride

hydrochloric acid

2-bromomethyl-1,3-dioxolane

→

1-(1,3-dioxolan-2-ylmethyl)-8-methylquinolin-2(1H)-one

Disolventes

N,N-dimethylformamide

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added under a nitrogen atmosphere
2. 2
   workup.STIRRINGthe mixture was stirred at 90° C. for 48 hours
3. 3
   TemperaturaThe reaction mixture was cooled to room temperature
4. 4
   OtroThe organic layer was separated
5. 5
   Extracciónthe aqueous layer was extracted with ethyl acetate
6. 6
   Lavadothe resultant solution was washed with an aqueous saturated sodium chloride solution
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Otrothe solvent was removed under reduced pressure
9. 9
   OtroThe residue thus obtained
10. 10
    Otrowas purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=8:1]

Procedimiento

To 3 mL of an N,N-dimethylformamide solution containing 0.17 g of 8-methylquinolin-2(1H)-one, 0.13 g of 60% sodium hydride was added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 30 minutes. Thereto was added 0.89 g of 2-bromomethyl-1,3-dioxolane, and the mixture was stirred at 90° C. for 48 hours. The reaction mixture was cooled to room temperature, then ethyl acetate and 1 mol/L hydrochloric acid were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=8:1] to obtain 0.18 g of a pale yellow oily substance, 1-(1,3-dioxolan-2-ylmethyl)-8-methylquinolin-2(1H)-one.

Fuente