Reacción #1509587

Ecuación de reacción

BF3

HCl

6-Chloro-2-methyl-nicotinonitrile

NaBH4

→

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

Disolventes

MeOH

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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)

Fuente