반응 #6900

반응 방정식

triethylamine

phosphorous oxychloride

4-nitroaniline

propionyl chloride

→

2-chloro-3-methyl-6-nitroquinoline

용매

N,N-dimethylformamide

chloroform

반응 조건

후처리

1. 1
   세척was washed with aq. 2N HCl
2. 2
   기타The organic layer was dried
3. 3
   여과filtered
4. 4
   기타the solvent removed under vacuum
5. 5
   기타to provide a solid
6. 6
   workup.ADDITIONthe above solid was added
7. 7
   기타The resulting reaction mixture
8. 8
   온도was heated at 75° for 12 h at which time the volatiles
9. 9
   기타were removed under vacuum
10. 10
    온도The residue was cooled in an ice bath
11. 11
    여과The resulting solids were filtered
12. 12
    세척washed with water
13. 13
    추출The solids were extracted with chloroform
14. 14
    기타dried
15. 15
    여과filtered
16. 16
    기타the solvent removed under vacuum
17. 17
    기타to afford the product, MS

실험 절차

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.

출처