Reaktion #6900

Reaktionsgleichung

triethylamine

phosphorous oxychloride

4-nitroaniline

propionyl chloride

→

2-chloro-3-methyl-6-nitroquinoline

Lösungsmittel

N,N-dimethylformamide

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwas washed with aq. 2N HCl
2. 2
   SonstigeThe organic layer was dried
3. 3
   Filtrationfiltered
4. 4
   Sonstigethe solvent removed under vacuum
5. 5
   Sonstigeto provide a solid
6. 6
   workup.ADDITIONthe above solid was added
7. 7
   SonstigeThe resulting reaction mixture
8. 8
   Temperaturwas heated at 75° for 12 h at which time the volatiles
9. 9
   Sonstigewere removed under vacuum
10. 10
    TemperaturThe residue was cooled in an ice bath
11. 11
    FiltrationThe resulting solids were filtered
12. 12
    Waschenwashed with water
13. 13
    ExtraktionThe solids were extracted with chloroform
14. 14
    Sonstigedried
15. 15
    Filtrationfiltered
16. 16
    Sonstigethe solvent removed under vacuum
17. 17
    Sonstigeto afford the product, MS

Vorschrift

To a solution of 4-nitroaniline (10 g, 72 mmol) in chloroform at 0° was added propionyl chloride (7 mL, 80 mol) followed by triethylamine (11.1 mL). The resulting solution was stirred for 2 h at r.t. at which time the reaction mixture was washed with aq. 2N HCl. The organic layer was dried filtered and the solvent removed under vacuum to provide a solid. A solution of phosphorous oxychloride (25 mL) and N,N-dimethylformamide (4.5 mL) was stirred at 0° for 0.15 h then the above solid was added. The resulting reaction mixture was heated at 75° for 12 h at which time the volatiles were removed under vacuum. The residue was cooled in an ice bath. To the cooled mixture was carefully added water (50 mL). The resulting solids were filtered and then washed with water. The solids were extracted with chloroform, the extracts were combined, dried, filtered and the solvent removed under vacuum to afford the product, MS: m/z 224 (MH+), which was used directly in the next step.

Quelle