Acetic Acid → 2-(4-Chloro-2,6-dimethyl-phenoxy)N4-(1-ethyl-propyl)-6-methyl-pyridine-3,4-diamine

Participants

Reaction Steps

A mixture of [2-(4-chloro-2,6-dimethyl-phenoxy)-6-methyl-3-nitro-pyridin-4-yl]-(1-ethyl-propyl)-amine (810 mg, 2.14 mmol) and iron (Fe) (594 mg, 10.72 mmol) in 96 ml of 1:1 of AcOH:H2O was heated at reflux for 2 hours. Additional Fe (600 mg) was added. The mixture was heated for an additional 1.5 hours. The reaction mixture was concentrated to dryness. The residue was quenched with water, basified to pH 9.0 and filtered through celite. The filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give the title compound as a yellow oil. The oil was purified through silica gel column chromatography using chloroform as eluent to give 570 mg of 2-(4-chloro-2,6-dimethyl-phenoxy)-N4-(1-ethyl-propyl)-6-methyl-pyridine-3,4-diamine as a tan solid, mp 72-74° C. 1H NMR (CDCl3) δ 7.04 (s, 2H), 6.11 (s, 1H), 4.03 (d, 1H), 3.30 (m, 1H), 3.07 (s, 1H), 2.14 (s, 3H), 2.10 (s, 6H), 1.4-1.75 (m, 4H), 0.97 (t, 6H) ppm. The corresponding di-HCl salt was prepared as a white solid, mp 208-210° C.

Provenance & Evidence