반응 #44980

반응 방정식

diisopropylamine

n-butyllithium n-hexane

4-chloropyridine

sodium hydroxide

dry ice acetone

→

4-chloronicotinic acid hydrochloride

용매

tetrahydrofuran

dry ice

tetrahydrofuran

반응 조건

후처리

1. 1
   온도cooling
2. 2
   온도same cooling conditions
3. 3
   workup.STIRRINGThe mixture is then stirred for 20 minutes under the
4. 4
   온도same cooling conditions
5. 5
   기타The resulting reaction solution
6. 6
   온도The reaction solution is cooled with ice
7. 7
   농축followed by concentration under reduced pressure
8. 8
   workup.DISSOLUTIONThe resulting residue is dissolved in water
9. 9
   세척washed with dichloromethane
10. 10
    온도The aqueous layer is cooled with ice
11. 11
    여과The precipitates are collected by filtration
12. 12
    기타dried

실험 절차

To a solution of diisopropylamine (20.0 g) in tetrahydrofuran (200 ml) is added dropwise 1.6 M n-butyllithium/n-hexane solution under ice-cooling. The mixture is then stirred for 30 minutes under the same cooling conditions. The reaction mixture is cooled with dry ice-acetone, and thereto is added dropwise a solution of 4-chloropyridine (20.4 g) in tetrahydrofuran (100 ml). The mixture is then stirred for 20 minutes under the same cooling conditions. The resulting reaction solution is poured in crushed dry ice in a portion and then warmed to room temperature. The reaction solution is cooled with ice and basified by addition of sodium hydroxide, followed by concentration under reduced pressure. The resulting residue is dissolved in water and washed with dichloromethane. The aqueous layer is cooled with ice and acidified with conc. hydrochloric acid. The precipitates are collected by filtration and dried to give 4-chloronicotinic acid hydrochloride (21.4 g).

출처