Acetic Acid → 2-Fluoro-5-nitroaniline

Participants

Reaction Steps

To a mixture of 40 ml of glacial acetic acid, 5 ml of water, and 8.32 g (0.0447 mole) of 2,4-dinitrofluorobenzene were added 0.10 g (0.00044 mole) of platinum oxide and 0.50 g (0.0090 mole) of powdered iron. Subsequently, 160 ml of ethanol was added to this mixture, and the entire reaction mixture was placed in a 500 ml Parr hydrogenation reactor. The reaction was stopped after 144 psi of hydrogen had been absorbed, and the reaction mixture was then filtered. The filtrate was evaporated under reduced pressure, and the residue was passed through a pad of silica gel, eluting with methylene chloride. The solvent was evaporated from the eluate under reduced pressure, producing 6.23 g of crude 2-fluoro-5-nitroaniline, m.p. 90°-92° C. Analysis of the nmr spectrum of this material showed it to be at least 85% pure 2-fluoro-5-nitroaniline.

Provenance & Evidence