Water → 6-[(4-chlorophenyl)sulfanyl]-3-pyridinylamine

Participants

Reaction Steps

6-(4-Chlorophenylthio)-3-nitropyridine (1.33 grams) was mixed with ammonium chloride (5.0 grams) in 5 ml. of water and about 50 ml. of 3A ethanol at 70°-80° C. Iron powder (3.0 grams) was added portionwise and the reaction mixture heated at 70°-80° C. with constant stirring, for 4 hours. The solution was filtered hot, solvents were removed, and the residue was washed with water; chloroform used to extract the compound was removed in vacuo. A thick oil was crystallized from ether-hexanes after passing through a flush with ethyl acetate on silica gel. The product precipitated as a white solid, yield 1.0 g., m.p. 55°-57°.

Provenance & Evidence