4-Aminopyridine → HCID 19890935, compound

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Reaction Steps

A solution of 4 g (0.0137 mol) 2-(2-picolylseleno)benzoic acid from Example 1 and 2 ml triethylamine in 40 ml dichloromethane is treated with 3.5 g (0.0137 mol) 2-chloro-1-methylpyridinium iodide and stirred at room temperature for 1 hour. Then a solution of 1.29 g (0.0137 mol) 4-aminopyridine and 2 ml triethylamine in 30 ml dichloromethane are added dropwise within 15 min and after stirring for 2 hours the reaction mixture is extracted once with 100 ml 1 N sodium hydroxide solution and twice with 100 ml portions of water. The organic phase is dried, the solvent removed and the residue taken up in 2-propanol (80 ml)/15% HCl (10 ml). After filtration the solid crude product is dissolved in 100 ml methanol and diethyl ether is added dropwise until the solution remains turbid. The crystals which then form are filtered off after 2 hours and dried.

Provenance & Evidence