반응 #57777

반응 방정식

HCl

NaOH

4-Cyanopyridine

AlCl3

4-chloroaniline

BCl3

→

(2-amino-5-chloro-phenyl)-pyridin-4-yl-methanone

수율 75.0%

용매

DCM

water

반응 조건

후처리

1. 1
   온도cooling, over a period of 15 min
2. 2
   workup.STIRRINGstirred for 30 min
3. 3
   온도The resulting solution was refluxed at 160° C. for 4 h
4. 4
   workup.STIRRINGstirred at room temperature overnight
5. 5
   온도the mixture was refluxed at 110° C. for 1.5 h
6. 6
   온도to cool down to room temperature
7. 7
   기타The resulting two layers were separated
8. 8
   추출the aqueous layer was extracted with DCM three times
9. 9
   건조dried over sodium sulfate
10. 10
    기타After removal of the solvent
11. 11
    세척the resulting solid was washed with ether

실험 절차

A solution of 4-chloroaniline (2.0 g, 16 mmol) in 30 mL of TCE was added drop wise to a solution of BCl3 (1M in DCM) (24 ml, 24 mmol) with ice bath cooling, over a period of 15 min and the reaction mixture stirred at that temperature for an additional 10 min. 4-Cyanopyridine (2.0 g, 19 mmol) and AlCl3 (3.0 g, 22 mmol) were added with ice-water cooling. The solution was allowed to warm to room temperature and stirred for 30 min. The resulting solution was refluxed at 160° C. for 4 h and stirred at room temperature overnight. The reaction mixture was then treated with 30 mL of 3N HCl and the mixture was refluxed at 110° C. for 1.5 h. The reaction mixture was allowed to cool down to room temperature and the solution was adjusted to pH12 with 6N NaOH and then diluted water and DCM. The resulting two layers were separated and the aqueous layer was extracted with DCM three times and the organic layers combined and dried over sodium sulfate. After removal of the solvent, the resulting solid was washed with ether to yield (2-amino-5-chloro-phenyl)-pyridin-4-yl-methanone (2.8 g, 75%).

출처