Water → 1-[4-(4-Amino-2-methylphenoxy)pyridin-2-yl]-3-(3-diethylaminopropyl)urea

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-diethylaminopropyl)-3-[4-(2-methyl-4-nitrophenoxy)pyridin-2-yl]urea (794 mg) in ethanol (50 ml) were added electrolytic iron powder (442 mg), ammonium chloride (847 mg) and water (10 ml), followed by stirring to heat at 90° C. for 1 hr. The reaction mixture was cooled down to room temperature, and filtered to remove an insoluble portion. The filtrate was concentrated under a reduced pressure to give a residue, which was then supplied with ethyl acetate (100 ml), washed with a saturated aqueous solution of sodium hydrogencarbonate, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 to 1:2, ethyl acetate, and then ethyl acetate:methanol=20:1 to 10:1) to provide the titled compound (110 mg, 15%).

Provenance & Evidence