Réaction #3622

Équation de réaction

4-nitrobenzoyl chloride

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

triethylamine

→

desired product

4,5-Dihydro-5-(4-nitrobenzoyl)pyrrolo[1,2-a]quinoxaline

Solvants

methylene chloride

ethyl acetate

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autrefollowed by ice bath
2. 2
   Températurecooling
3. 3
   workup.ADDITIONaddition
4. 4
   Autrethe ice bath is removed
5. 5
   AutreThe volatiles are removed in vacuo
6. 6
   Autreto give a residue which
7. 7
   LavageThe solution is washed with water, 1N HCl, NaHCO3, and brine
8. 8
   SéchageThe reaction mixture is dried with Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Autreevaporated in vacuo
11. 11
    Autreto give a solid which
12. 12
    Autreis purified by flash chromatography

Mode opératoire

To a solution of 5 mmol of 4,5-dihydropyrrolo[1,2-a]quinoxaline in 50 ml of methylene chloride under argon is added 10 mmol of triethylamine followed by ice bath cooling. A solution of 5 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition, the ice bath is removed and the reaction mixture stirred at room temperature for 2 hours. The volatiles are removed in vacuo to give a residue which is dissolved in ethyl acetate. The solution is washed with water, 1N HCl, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography to give the desired product (from ethyl acetate) as a solid, m.p. 174°-178° C.

Source