Ammonium Chloride → 2-Chloro-5-iodoaniline

Participants

Reaction Conditions

Reaction Steps

To 1-chloro-4-iodo-2-nitrobenzene (1.27 g, 4.49 mmol) in methanol (20 ml) was added iron powder (1.25 g, 22 mmol) and the reaction heated to 50° C. A solution of ammonium chloride (1.92 g, 36 mmol) in water (10 ml) was added slowly and the reaction heated to 70° C. overnight. Reaction was cooled, filtered through celite, washed with methanol and solvent reduced in vacuo. The residue was purified by chromatography on silica gel (gradient of hexane to 10% ethyl acetate in hexane) to afford the title compound. MS (ES+) m/e 254 [M+H]+.

Provenance & Evidence