반응 #710502

반응 방정식

NaBH4

BF3

2-Chloro-3-[(E)-2-nitrovinyl]-6-(trifluoromethyl)pyridine

→

hydrochloride

수율 58.3%

2-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]ethanamine

용매

HCl

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타The resulting reaction mixture
2. 2
   기타was allowed to room temperature
3. 3
   workup.ADDITIONwas added to above reaction mixture at room temperature
4. 4
   기타The resulting reaction mixture
5. 5
   기타was allowed to room temperature
6. 6
   workup.STIRRINGstirred for 16 h
7. 7
   기타After completion of reaction
8. 8
   기타the reaction mixture was quenched in ice water (200 mL)
9. 9
   추출extracted with ethyl acetate (3×200 mL)
10. 10
    세척The combined organic layers were washed with water (1×100 mL), brine (1×100 mL)
11. 11
    건조dried over anhydrous sodium sulfate
12. 12
    기타the solvent was removed under reduced pressure
13. 13
    기타to get crude amine
14. 14
    workup.STIRRINGstirred at room temperature for 2.0 h
15. 15
    농축The reaction mixture was concentrated under reduced pressure

실험 절차

To a stirred solution of NaBH4 (16.0 g, 4.2 eq.) in tetrahydrofuran (125 mL) was added BF3 etherate (125 mL) at 0° C. The resulting reaction mixture was allowed to room temperature and stirred for 15 min 2-Chloro-3-[(E)-2-nitrovinyl]-6-(trifluoromethyl)pyridine (Int-19) (25.0 g, 1.0 eq) in tetrahydrofuran (125 mL) was added to above reaction mixture at room temperature. The reaction mixture was heated to 70° C. and stirred for 2 h. The resulting reaction mixture was allowed to room temperature and stirred for 16 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was quenched in ice water (200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water (1×100 mL), brine (1×100 mL), dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to get crude amine. The amine compound was dissolved in ethanolic HCl (50 mL) and stirred at room temperature for 2.0 h. The reaction mixture was concentrated under reduced pressure to get crude 2-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]ethanamine (IIb-35) hydrochloride (15.0 g, 58.3%).

출처