N-methyl-2-pyrrolidone → 3-Aminopyridine-2-carbonitrile

Participants

Reaction Steps

A mixture of 3-Amino-2-chloropyridine (5 g) and cuprous cyanide (5g) in 10 mL of N-Methylpyrrolidone was heated with stirring at 185° C. for 2h under an atmosphere of nitrogen. The reaction mixture was concentrated in vacuo and concentrated ammonium hydroxide and 10% methanol/methylene chloride were added. The mixture was shaken and filtered, the organic layer separated and the aqueous layer extracted two times with methanol/methylene chloride. The combined organic extracts were dried over magnesium sulfate and the solvent removed in vacuo. The residue was recrystallized from ethyl acetate/hexane to afford 3-Amino-2-cyanopyridine as a tan solid.

Provenance & Evidence