Nitroethane → Amphetamine

Participants

Reaction Steps

A mixture of 7.56 g (50 mmol) of 3-nitrobenzaldehyde, 11.25 g (150 mmol) of nitroethane and 4.24 g (55 mmol) of ammonium acetate was heated in 2 mL of acetic acid in a 110° C. oil bath for 2 1/2 hours. Subsequent examination of the mixture by preparative thin layer chromatography with hexane/ethyl acetate showed almost no starting material remaining. Volatile materials were removed with a rotary evaporator, and the residue was partitioned between dichloromethane and water, with washing of the organic layer twice with 10% sodium bicarbonate. Caution was necessary because gas evolution occurred during the first bicarbonate wash. Drying was performed with magnesium sulfate. Filtration and removal of solvent left 9.13 g of crude product. Half of this was chromatographed on a 3×35 cm flash silica column, packed with hexane and eluted with 7:1 hexane/ethyl acetate to give 1.66 g (32%) of pure title compound.

Provenance & Evidence