2-CYANO-4-METHYL-5-NITROPYRIDINE

2-Bromo-4-methyl-5-nitropyridine (104 g, 0.479 mol), Zn(CN)2 (79 g, 0.673 mol, 1.4 eq. ), and Pd (PPh3)4 0.023 mol, 5 molpercent) were added to a round bottom flask. NOTE: Using catalyst purchased from STREM resulted in shorter reaction times and better yields. DMF (900 mL) was degassed for 10 min before adding to the solid mixture. The mixture was heated in an oil bath to an inside temp of 80° C. The color changed from light yellow to light brown as the inside temperature reached 80° C. The mixture was stirred at the same temperature for 3 h, and monitored by TLC. The solvent was removed in vacuo. The residue was dissolved in a mixture of dichloromethane and water, and insoluble material was removed by filtration through Celite. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried (magnesium sulfate), and concentrated. The residue was purified by column chromatography starting with 100percent hexanes to hexanes/ethyl acetate 4: 1. Recrystallization from hexanes yielded 65.8 g (83percent) of the desired product. To a solution of 2-bromo-4-methyl-5-nitropyridine (5.0 g, 23 mmol) in 20 ml of THF, were added Zn(CN)To a stirred solution of the 4-methyl-5-nitropyridin-2-yl trifluoromethanesulfonate (8.65 g, 30.2 mmol) in DMF (200 mL) was added zinc cyanide (3.53, 30.2 mmol) followed by Pd (PPh3)4 g, 1.7 mmol). The mixture was degassed for 10 min. The solution was heated to 80° C for 18 h. The solvent was removed in vacuo. The residue was dissolved in a mixture of dichloromethane and water, and insoluble material was removed by filtration through Celite. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried (magnesium sulfate), and concentrated. The residue was purified by column chromatography starting with 100percent hexanes to hexane/ethyl acetate 4:1. Recrystallization from hexanes yielded 4.43 g (90percent) of the desired product.

Molecular Weight:163.13
XLogP3:1.1
Hydrogen Bond Acceptor Count:4
Exact Mass:163.038176411
Monoisotopic Mass:163.038176411
Topological Polar Surface Area:82.5
Heavy Atom Count:12
Complexity:227
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes