Methanesulfonic Acid → decyl nicotinate N-oxide

Participants

Reaction Steps

Nicotinic acid N-oxide (5.00 g, 36 mmol), decyl alcohol (5.86 g, 37 mmol) and methanesulfonic acid (3.70 g, 38.5 mmol) were stirred and heated to reflux in toluene (50 mL), in a flask equipped with a condenser and a Dean-Stark trap for 19 hours. The rection mixture was then cooled, diluted with ether and washed successively with water, aqueous sodium bicarbonate and brine. The toluene/ether solution was then dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was recrystallized from ligroine (100 mL) to give 7.50 g (27 mmol) of decyl nicotinate N-oxide, mp 80.5° C.

Provenance & Evidence