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

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Reaction Steps

The solution of 2-Methyl-5-(2-methyl-4-nitro-phenoxy)-pyridine (6.4 g, 26.2 mmol), 10 wt % Pd/C (0.50 g) in ethanol (100 mL) was stirred under 1 atm hydrogen at rt for 24 h. Then the Pd/C catalyst was removed by filtration through a layer of celite. Removal of the solvent gave the desired product as an off-white solid (5.55 g, 99%). 1H-NMR (DMSO-d6) δ 8.04 (d, J=2.7 Hz, 1H), 7.13 (d, J=5.4 Hz, 1H), 7.02 (dd, J=8.7, 3.1 Hz, 1H), 6.68 (d, J=8.7 Hz, 1H), 6.49 (d, J=2.6 Hz, 1H), 6.42 (dd, J=8.4, 2.8 Hz, 1H), 4.96 (br, 2H), 2.39 (s, 3H), 1.97 (s, 3H). LCMS RT=1.04 min; [M+H]+=215.2.

Provenance & Evidence