Dimethyl Sulfoxide → Methyl 6-(azidomethyl)nicotinate

Participants

Reaction Conditions

Reaction Steps

Add 6-chloromethyl-nicotinic acid methyl ester (9.1 g, 40.98 mmol) and dimethylsulfoxide (100 mL) into a flask and cool to 0° C. Add sodium azide (4 g, 61.47 mmol) and sodium carbonate (13 g, 122.9 mmol) to the reaction mixture. Let the mixture slowly warm to room temperature. Stir for 1 hr at room temperature. Add water (100 mL) to the mixture. Extract with diethyl ether (100 mL×3). Wash the organic layer with water and brine. Dry with sodium sulfate. Remove solvent under reduced pressure to give the product (6.8 g, 86% yield) as light yellow oil. MS (m/z): 193.3 (M+1).

Provenance & Evidence