2-Methyl-5-(2-methyl-4-nitrophenoxy)pyridine → 3-Methyl-4-((6-methylpyridin-3-yl)oxy)aniline

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A mixture of 2-methyl-5-(2-methyl-4-nitro-phenoxy)-pyridine (11.5 g, 47.1 mmol) and palladium on carbon (300 mg, 10 wt. %, wet) in MeOH (200 mL) was flashed with hydrogen. A hydrogen balloon was then applied to the reaction mixture. The reaction was stirred for 2 hours and the solution was filtered through a pad of celite, and the pad was washed with MeOH (300 mL). Concentration of the solution gave crude product (8.8 g, 87%) as light yellow solid.

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