2-Ethoxy-1-methoxy-4-nitro-benzene → 3-Ethoxy-4-methoxyaniline

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Reaction Steps

A mixture of 2-ethoxy-1-methoxy-4-nitrobenzene (1.5 g, 7.6 mmol) and 5% Pd—C (0.3 g) in 30 mL of ethyl acetate was hydrogenated under 50 psi of hydrogen gas for 14 hours. The mixture was filtered through Celite and the filtrate was evaporated, providing 1.25 g of the product, in 98% yield: 1H NMR (CDCl3) δ 1.44 (t, J=7.0 Hz, 3H), 3.27 (br, 2H), 3.79 (s, 3H), 4.04 (q, J=7.0 Hz, 2H), 6.90 (d, J=8.9 Hz, 1H), 7.74 (d, J=2.5 Hz, 1H), 7.90 (dd, J=8.9 Hz, J=2.5 Hz, 1H).

Provenance & Evidence