6-(4,5-Dimethoxy-2-nitrophenyl)-2,3-dimethoxynaphthalene → 2-(6,7-Dimethoxynaphthalen-2-yl)-4,5-dimethoxyaniline

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Reaction Steps

6-(4,5-Dimethoxy-2-nitrophenyl)-2,3-dimethoxynaphthalene (12 mg, 0.03 mmol) was hydrogenated overnight in ethyl acetate (20 mL) at 40-45 lb./sq. in. under catalysis of palladium (10 wt % on activated carbon, 10 mg). The solution was passed through celite bed and the catalyst was washed with ethyl acetate (3×10 mL). Concentration in vacuo gave the crude product. Chromatography using 65:35 hexanes:ethyl acetate gave compound 18 (11 mg) in nearly 100% yield; 1H NMR (CDCl3) d 3.84(3H, s), 3.89(3H, s), 4.01(3H, s), 4.02(3H, s), 6.41(1H, s), 6.80(1H, s), 7.14(1H, s), 7.15(1H, s), 7.43(1H, dd, J=8.4, J=1.6), 7.75(1H, d, J=1.5), 7.75(1H, d, J=8.4); 13C NMR d 56.4, 57.2, 101.3, 106.6, 106.8, 115.2, 119.9, 126.2, 126.8, 127.3, 128.5, 129.9, 135.7, 138.0, 142.7, 149.8, 150.1, 150.3.

Provenance & Evidence