Réaction #1509587

Équation de réaction

BF3

HCl

6-Chloro-2-methyl-nicotinonitrile

NaBH4

→

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

Solvants

MeOH

THF

Conditions de réaction

Traitement

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

Mode opératoire

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)

Source