반응 #1509587

반응 방정식

BF3

HCl

6-Chloro-2-methyl-nicotinonitrile

NaBH4

→

C-(6-Chloro-2-methyl-pyridin-3-yl)-methylamine

용매

MeOH

THF

반응 조건

후처리

1. 1
   온도refluxed for 1 h
2. 2
   기타The organic solvent was removed in vacuum and conc. NaOH (40 ml)
3. 3
   workup.ADDITIONwas added
4. 4
   추출followed by extraction with diethyl ether
5. 5
   기타The organic layer was separated
6. 6
   기타dried
7. 7
   농축concentrated in vacuum
8. 8
   여과followed by filtration over silica gel (EtOAc/MeOH 80:20)
9. 9
   기타The title compound was crystallized from MeOH/HCl (5.5 g)

실험 절차

To a solution of 6-Chloro-2-methyl-nicotinonitrile (6 g) in THF (120 ml) at 25° C. was added NaBH4 (3 g) followed by the dropwise addition of BF3 etherate (6 ml). The reaction mixture was stirred for 3 h. MeOH (100 ml) and 2N HCl (100 ml) was added and refluxed for 1 h. The organic solvent was removed in vacuum and conc. NaOH (40 ml) was added followed by extraction with diethyl ether. The organic layer was separated, dried and concentrated in vacuum followed by filtration over silica gel (EtOAc/MeOH 80:20). The title compound was crystallized from MeOH/HCl (5.5 g)

출처