Reacción #6900

Ecuación de reacción

triethylamine

phosphorous oxychloride

4-nitroaniline

propionyl chloride

→

2-chloro-3-methyl-6-nitroquinoline

Disolventes

N,N-dimethylformamide

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowas washed with aq. 2N HCl
2. 2
   OtroThe organic layer was dried
3. 3
   Filtraciónfiltered
4. 4
   Otrothe solvent removed under vacuum
5. 5
   Otroto provide a solid
6. 6
   workup.ADDITIONthe above solid was added
7. 7
   OtroThe resulting reaction mixture
8. 8
   Temperaturawas heated at 75° for 12 h at which time the volatiles
9. 9
   Otrowere removed under vacuum
10. 10
    TemperaturaThe residue was cooled in an ice bath
11. 11
    FiltraciónThe resulting solids were filtered
12. 12
    Lavadowashed with water
13. 13
    ExtracciónThe solids were extracted with chloroform
14. 14
    Otrodried
15. 15
    Filtraciónfiltered
16. 16
    Otrothe solvent removed under vacuum
17. 17
    Otroto afford the product, MS

Procedimiento

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.

Fuente