反応 #6900

反応方程式

triethylamine

phosphorous oxychloride

4-nitroaniline

propionyl chloride

→

2-chloro-3-methyl-6-nitroquinoline

溶媒

N,N-dimethylformamide

chloroform

反応条件

後処理

1. 1
   洗浄was washed with aq. 2N HCl
2. 2
   その他The organic layer was dried
3. 3
   ろ過filtered
4. 4
   その他the solvent removed under vacuum
5. 5
   その他to provide a solid
6. 6
   workup.ADDITIONthe above solid was added
7. 7
   その他The resulting reaction mixture
8. 8
   温度was heated at 75° for 12 h at which time the volatiles
9. 9
   その他were removed under vacuum
10. 10
    温度The residue was cooled in an ice bath
11. 11
    ろ過The resulting solids were filtered
12. 12
    洗浄washed with water
13. 13
    抽出The solids were extracted with chloroform
14. 14
    その他dried
15. 15
    ろ過filtered
16. 16
    その他the solvent removed under vacuum
17. 17
    その他to afford the product, MS

実験手順

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.

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