Reaktion #67975

Reaktionsgleichung

N,N-dimethylformamide

sodium hydride

imidazole

7-bromo-1-(1,3-dioxolan-2-ylmethyl)-4-methylquinolin-2(1H)-one

N,N-dimethylformamide

→

1-(1,3-dioxolan-2-ylmethyl)-7-(1H-imidazol-1-yl)-4-methylquinolin-2(1H)-one

Lösungsmittel

water

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   workup.STIRRINGstirred for 40 minutes
3. 3
   workup.STIRRINGthe mixture was further stirred for 1 hour
4. 4
   TemperaturThe reaction mixture was cooled to room temperature
5. 5
   Filtrationthe insoluble material filtered off
6. 6
   SonstigeThe organic layer was separated
7. 7
   Extraktionthe aqueous layer was extracted with chloroform
8. 8
   Trocknenthe resultant solution was dried over anhydrous magnesium sulfate
9. 9
   Sonstigethe solvent was removed under reduced pressure
10. 10
    SonstigeThe residue thus obtained
11. 11
    Sonstigewas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

Vorschrift

To 0.7 mL of an N,N-dimethylformamide solution containing 74 mg of 60% sodium hydride, 0.14 g of imidazole was added at room temperature, and the mixture was stirred for 10 minutes. Thereto were added 0.20 g of 7-bromo-1-(1,3-dioxolan-2-ylmethyl)-4-methylquinolin-2(1H)-one and 17 mg of copper(II) oxide, and the mixture was heated to 140 to 145° C. and stirred for 40 minutes. Thereto was further added 2 mL of N,N-dimethylformamide, and the mixture was further stirred for 1 hour. The reaction mixture was cooled to room temperature, then chloroform and water were added thereto, and the insoluble material filtered off. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1] to obtain 77 mg of a brown oily substance, 1-(1,3-dioxolan-2-ylmethyl)-7-(1H-imidazol-1-yl)-4-methylquinolin-2(1H)-one.

Quelle