Reaction #1509587

Reaction equation

BF3

HCl

6-Chloro-2-methyl-nicotinonitrile

NaBH4

→

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

Solvents

MeOH

THF

Conditions

Workup

1. 1
   Temperaturerefluxed for 1 h
2. 2
   OtherThe 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
   OtherThe organic layer was separated
6. 6
   Otherdried
7. 7
   Concentrationconcentrated in vacuum
8. 8
   Filtrationfollowed by filtration over silica gel (EtOAc/MeOH 80:20)
9. 9
   OtherThe title compound was crystallized from MeOH/HCl (5.5 g)

Procedure

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