Sulfuric Acid → 1-(2-nitrobenzyl)pyrrolidine

Participants

Reaction Steps

To a solution of the crude 2-nitrobenzyl bromide (185 g, containing approximately 21% by weight of the 2-nitrobenzyl bromide (approximately 39 g, 180 mmol) besides the starting material 2-nitrotoluene and by-products of its bromination such as 2-nitrobenzal bromide) in chlorobenzene were added methylene chloride (500 ml) and pyrrolidine (28.1 g, 395 mmol). The solution was stirred at room temperature overnight. Then, the solution was cooled to 0° C. and aqueous solution of H2SO4 (200 g, 10% per weight) were added. The aqueous phase was extracted four times with methylene chloride (30 ml each). The aqueous phase was then treated with saturated aqueous solution of K2CO3 until the gas evolution had ceased. Then, it was extracted four times with methylene chloride (30 ml each). The combined organic phases were washed with water and brine and dried over MgSO4 affording a yellow liquid (yield: 89%). The product obtained was sufficient pure (>95%) for subsequent steps without further purification.

Provenance & Evidence