Water → 2-Iodo-4-methyl-6-nitroaniline

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Reaction Steps

A solution of 4-amino-3-nitrotoluene (30.4 g) in acetic acid (250 ml) was refluxed with iodine monochloride (65.0 g) for 7 h with stirring, then was cooled and added to excess water. The precipitate was filtered off, washed with aqueous sodium sulfite and after column chromatography yielded 4-amino-3-iodo-5-nitrotoluene (14.2 g). δ (360 MHz, DMSO-d6) 2.19 (3H, s, CH3), 6.88 (2H, bs, NH2), 7.88 (1H, d, 2-H) and 7.94 (1H, d, 6-H).

Provenance & Evidence