Hydrochloric Acid → 4-(2-(Diethylamino)ethoxy)aniline

Participants

Reaction Steps

N,N-Diethyl-2-(4-nitrophenoxy)ethylamine (4.0 g) (prepared by the method described in Helv. Chim. Acta. 1960, 43, 1971) was dissolved in IMS (70 ml), water (10 ml) and concentrated hydrochloric acid (2 ml). The mixture was boiled under reflux and then reduced iron powder (4.6 g) was carefully added in portions. The mixture was boiled under reflux for 7 hours then hot filtered. The filtrate was basified with 5M sodium hydroxide solution and then evaporated under reduced pressure. The residue was partitioned between water and ether. The organic layer was separated, dried and evaporated to give 4-[2-(N,N-diethylamino)ethoxy]aniline as an oil.

Provenance & Evidence