反应 #710502

反应方程式

NaBH4

BF3

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

→

hydrochloride

收率 58.3%

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

溶剂

HCl

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   其他The resulting reaction mixture
2. 2
   其他was allowed to room temperature
3. 3
   workup.ADDITIONwas added to above reaction mixture at room temperature
4. 4
   其他The resulting reaction mixture
5. 5
   其他was allowed to room temperature
6. 6
   workup.STIRRINGstirred for 16 h
7. 7
   其他After completion of reaction
8. 8
   其他the reaction mixture was quenched in ice water (200 mL)
9. 9
   萃取extracted with ethyl acetate (3×200 mL)
10. 10
    洗涤The combined organic layers were washed with water (1×100 mL), brine (1×100 mL)
11. 11
    干燥dried over anhydrous sodium sulfate
12. 12
    其他the solvent was removed under reduced pressure
13. 13
    其他to get crude amine
14. 14
    workup.STIRRINGstirred at room temperature for 2.0 h
15. 15
    浓缩The reaction mixture was concentrated under reduced pressure

实验过程

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%).

来源