반응 #736772

반응 방정식

ethyl 4-chloro-6-ethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate

4-chlorophenylhydrazine

→

2,3,6,7,8,9-hexahydro-2-p-chlorophenyl-8-ethylpyrazolo[4,3-c]quinolin-3-(5H)-one

용매

NaOH

n-butanol

반응 조건

후처리

1. 1
   온도the reaction mixture is heated
2. 2
   온도at reflux for 41/2 hours
3. 3
   온도The reaction mixture is cooled to room temperature
4. 4
   여과the precipitate is filtered off
5. 5
   세척washed with hexane
6. 6
   기타air-dried
7. 7
   기타to yield a yellow solid
8. 8
   추출extracted with ether
9. 9
   workup.ADDITIONThe aqueous layer is then treated with 1.6 g of NH4Cl
10. 10
    여과The precipitate which forms is filtered off
11. 11
    세척washed with water
12. 12
    기타dried in a vacuum oven at 120° overnight

실험 절차

A solution of 2.6 g of ethyl 4-chloro-6-ethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate in 30 ml n-butanol is treated with 1.38 g of 4-chlorophenylhydrazine at room temperature under nitrogen. After stirring at room temperature overnight, the reaction mixture is heated at reflux for 41/2 hours. The reaction mixture is cooled to room temperature, the precipitate is filtered off, washed with hexane and air-dried to yield a yellow solid. The crude product is dissolved in 30 ml 1N NaOH and extracted with ether. The aqueous layer is then treated with 1.6 g of NH4Cl. The precipitate which forms is filtered off, washed with water, and dried in a vacuum oven at 120° overnight to yield 2,3,6,7,8,9-hexahydro-2-p-chlorophenyl-8-ethylpyrazolo[4,3-c]quinolin-3-(5H)-one, m.p. 318°-320°.

출처