Methyl iodide → 4-Pyridinecarbaldehyde oxime

Participants

Reaction Steps

A solution of 4-pyridinecarboxaldehyde oxime, hydrochloride (24.5 g, 154 mmol) in 250 ml of water was treated with solid sodium bicarbonate (13 g, 155 mmol) and the resulting oil was extracted into 1.2 l of ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and calcium sulfate, and concentrated to 500 ml of solution in vacuo. This concentrate was treated with iodomethane (21.5 ml, 344 mmol) and heated with 100 ml of acetonitrile under reflux for two hours. The resulting yellow salt which separated was collected by filtration and dried to provide 35.8 g of 4-pyridinecarboxaldehyde oxime, methiodide, mp 180°-182° C.

Provenance & Evidence