反応 #710502

反応方程式

NaBH4

BF3

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

→

hydrochloride

収率 58.3%

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

溶媒

HCl

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

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

実験手順

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%).

出典