3-Cyano-2,6-dichloro-4-methylpyridine → 4-Methyl-3-cyanopyridine

Referring to JP-A-7-10841, 2,6-dichloro-4-methylnicotinonitrile (manufactured by Mabridge) (17.0 g, 90.9 mmol) was dissolved in methanol (450 ml), and 10% Pd—C (1.7 g, 10 wt. %) and sodium acetate (15.2 g, 186 mmol) were added. The mixture was stirred at room temperature under hydrogen pressure for 16 hrs. and the catalyst and the like were filtered off. The solvent was concentrated under reduced pressure, and the resulting mixture was partitioned between dichloromethane (300 ml)-5% aqueous sodium hydrogen carbonate (200 ml). The organic layer was dried and the resulting mixture was concentrated under reduced pressure. Recrystallization from a small amount of isopropyl ether gave the title compound (9.2 g, 86%).

1. filtrationand the catalyst and the like were filtered off
2. concentrationThe solvent was concentrated under reduced pressure
3. customthe resulting mixture was partitioned between dichloromethane (300 ml)-5% aqueous sodium hydrogen carbonate (200 ml)
4. customThe organic layer was dried
5. concentrationthe resulting mixture was concentrated under reduced pressure
6. customRecrystallization from a small amount of isopropyl ether

ORD record

ord-296b1055552f46cba6a7c18b8ccdbb12

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067537B2