Ammonium Chloride → 4-(2-Chloro-5-pyridylmethyloxy)aniline

Participants

Reaction Steps

Two grams (7.6 mmol) of 2-chloro-5-(4-nitrophenoxy) methylpyridine and 4 grams (76.0 mmol) of ammonium chloride in 40 ml of ethanol and 20 ml of water are heated to 60°, after which 2.1 grams (38.0 mmol) of iron powder is added in small portions over 15 minutes. The mixture is heated under reflux for 2 hours. The reaction is cooled and stripped, and the residue is taken up in ether, washed with water, dried over sodium sulfate and stripped to yield 2-chloro-5-(4-aminophenoxy)methylpyridine.

Provenance & Evidence