Pyridine → 3-Iodo-4,5-dimethoxybenzonitrile

Participants

Reaction Steps

A mixture of 5.0 g of 3-iodo-4,5-dimethoxy-benzaldehyde, 1.18 g of hydroxylamine hydrochloride, 1.37 g of pyridine and 17 ml of toluene is held at reflux for 2 hrs. (see A. Saednya, Synthesis 1982, 190). The precipitate which separates after cooling is filtered off under suction. Chromatography on silica gel with methylene chloride/methanol 9:1 yields 3.09 g of 3-iodo-4,5-dimethoxy-benzonitrile as a colourless solid. Yield: 63%. Mass spectrum: peaks inter alia at m/e: 289 (100%), 274 (38%), 132 (30%), 119 (43%).

Provenance & Evidence