Methylamine → 6-Chloro-N-methyl-3-pyridinemethanamine

Participants

Reaction Steps

A mixture of 15.05 g of 2-chloro-5-(chloromethyl)pyridine and 50 ml of acetonitrile was added dropwise to a mixture of 36 g of 40% aqueous methylamine solution and 200 ml of acetonitrile over a period of 1 hour at room temperature and the whole mixture was further stirred for 90 minutes. The reaction mixture was concentrated and the residue was diluted with 100 ml of water, neutralized with sodium hydrogen carbonate, saturated with sodium chloride and extracted with dichloromethane (200 ml×2). The organic solution was dried over anhydrous magnesium sulfate and concentrated and the residue was purified by column chromatography (eluent: dichloromethane-methanol (4:1)) to give 8.77 g of 2-chloro-5-(methylaminomethyl)pyridine as a yellow brown liquid.

Provenance & Evidence