Benzyl Chloride → 2-Amino-3-benzyloxypyridine

Participants

Reaction Conditions

Reaction Steps

In a 12 liter 3-neck round bottom flask equipped with a mechanical stirrer and thermometer there were placed 2.5 liters of 40% sodium hydroxide solution, 26.5 g of Adogen 464 (Reg. Trademark) and 2.5 liters of dichloromethane. To this vigorously stirred mixture was added 550 g of 2-amino-3-hydroxypyridine. The temperature was 38° C. The brown orange mixture was cooled to 25° C., and 677.5 g of benzylchloride was added in one portion, stirred 16 hr. and the mixture was allowed to separate into 2 phases. The lower aqueous phase was separated and diluted with 1 liter of ice:water. This solution was then extracted with dichloromethane (3×15 liters). The combined dichloromethane extractswere added to the original dichloromethane phase, washed with 1 liter of saturated sodium chloride solution and dried over potassium carbonate. Thedichloromethane extract was filtered and concentrated on the rotary evaporator to an orange solid. This solid was dissolved in 1 liter of boiling absolute ethanol, and the solution was filtered. The filtrate was chilled, and the crystals that formed were filtered, washed with 500 ml ofethanol at -10° C., and dried at 50° C. in a vacuum oven, to give the desired product.

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