反応 #1509587

反応方程式

BF3

HCl

6-Chloro-2-methyl-nicotinonitrile

NaBH4

→

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

溶媒

MeOH

THF

反応条件

後処理

1. 1
   温度refluxed for 1 h
2. 2
   その他The organic solvent was removed in vacuum and conc. NaOH (40 ml)
3. 3
   workup.ADDITIONwas added
4. 4
   抽出followed by extraction with diethyl ether
5. 5
   その他The organic layer was separated
6. 6
   その他dried
7. 7
   濃縮concentrated in vacuum
8. 8
   ろ過followed by filtration over silica gel (EtOAc/MeOH 80:20)
9. 9
   その他The title compound was crystallized from MeOH/HCl (5.5 g)

実験手順

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)

出典