Sodium Hydroxide → 2,4-Dichloro-m-toluidine

Participants

Reaction Steps

A stirred solution of 50.0 g (0.243 mole) of 2,6-dichloro-3-nitrotoluene and 225 g (1.0 mole) of stannous chloride in 250 ml of concentrated hydrochloric acid and 125 ml of ethanol was heated under reflux for 1 hour. The reaction mixture was allowed to cool to ambient temperature and was stirred for 16 hours, made basic with sodium hydroxide, and concentrated under reduced pressure. The residue was slurried with water and the insolubles were collected by filtration and allowed to air dry. The solid was digested with 500 ml of chloroform and 100 ml of ethanol. The mixture was filtered and the filtrate concentrated under reduced pressure to give 33.5 g of 2,4-dichloro-3-methylaniline, m.p. 56°-57.5° C. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence