Reaktion #1509587

Reaktionsgleichung

BF3

HCl

6-Chloro-2-methyl-nicotinonitrile

NaBH4

→

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

Lösungsmittel

MeOH

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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)

Quelle