(6-Methyl-3-nitro-2-phenoxypyridin-4-yl)-{2-[3-(pyridin-3-yl)propoxy]ethyl}amine → 6-methyl-2-phenoxy-N4-{2-[3-(pyridin-3-yl)propoxy]ethyl}pyridine-3,4-diamine

Participants

Reaction Steps

Under a nitrogen purge, 5% platinum on carbon (2.0 g), toluene (5 mL), and 2-propanol (5 mL) were added to a Parr vessel. A solution of (6-methyl-3-nitro-2-phenoxypyridin-4-yl)-{2-[3-(pyridin-3-yl)propoxy]ethyl}amine (5.71 g, 14.0 mmol) in toluene (45 mL) was then added. The vessel was placed under hydrogen pressure (49 psi, 3.4×105 Pa) for three hours. An analysis by liquid chromatography/mass spectrometry indicated the presence of starting material, and additional 5% platinum on carbon (0.1 g) was added. The reaction was continued for an additional 6 hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure to yield 5.2 g of 6-methyl-2-phenoxy-N4-{2-[3-(pyridin-3-yl)propoxy]ethyl}pyridine-3,4-diamine as a dark oil.

Provenance & Evidence