4-(Chloromethyl)pyridinium chloride → HCID 70087909, compound

Participants

Reaction Steps

To a solution of N-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-malonamic acid methyl ester (0.95 g, 3.7 mmol) in methanol (7 ml), sodium methoxide (0.20 g, 3.7 mmol) was added, and the mixture was stirred for 1 hour at ambient temperature. 4-Picolylchloride (0.53 g, 4.1 mmol of freshly liberated free base from 4-picolyl chloride hydrochloride; Aldrich Chemical Co.) was added, and the reaction was then stirred for 18 hours at ambient temperature. Ethyl acetate and water (15 ml of each) were added, and the mixture was well shaken. The separated aqueous extracted was then extracted with an equal volume portion of fresh ethyl acetate. The combined organic extracts were dried (anhydrous sodium sulfate), and concentrated in vacuo to an orange oil (1.16 g). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with initially ethyl acetate and subsequently with methanol/ethyl acetate up to a 1:4 ratio, respectively, in volume) afforded the title compound (12 mg) as an oil.

Provenance & Evidence