Reaktion #83426

Reaktionsgleichung

4-[(2-methylbenzoyl)amino]benzoyl chloride

1,1'-carbonyldiimidazole

4,5-dihydropyrrolo-[1,2-a]-quinoxaline

→

desired product

Ausbeute 34.4%

2-Methyl-N-[4-(pyrrolo[1,2-a]quinoxalin-5 (4H)-ylcarbonyl)phenyl]benzamide

Ausbeute 34.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby heating
2. 2
   Temperaturat reflux for 60 hours
3. 3
   EinengenThe volatiles are concentrated vacuo to a residue which
4. 4
   workup.DISSOLUTIONis dissolved in ethyl acetate
5. 5
   WaschenThe organic layer is washed with 1N HCl, 1M NaHCO3, brine
6. 6
   Trocknendried with Na2SO4
7. 7
   Filtrationfiltered through hydrous magnesium silicate
8. 8
   EinengenThe volatiles are concentrated in vacuo to a residue which
9. 9
   Sonstigeis chromatographed by elution with 1:2 ethyl acetate-hexanes

Vorschrift

A mixture of 0.51 g of 4-[(2-methylbenzoyl)amino]benzoyl chloride and 0.36 g of 1,1'-carbonyldiimidazole in 6 ml of tetrahydrofuran is stirred at room temperature for 1 hour. To the reaction mixture is added 0.17 g of 4,5-dihydropyrrolo-[1,2-a]-quinoxaline followed by heating at reflux for 60 hours. The volatiles are concentrated vacuo to a residue which is dissolved in ethyl acetate. The organic layer is washed with 1N HCl, 1M NaHCO3, brine, dried with Na2SO4 and filtered through hydrous magnesium silicate. The volatiles are concentrated in vacuo to a residue which is chromatographed by elution with 1:2 ethyl acetate-hexanes to give 0.14 g of the desired product as a white solid, m.p. 206°-207° C.;

Quelle