[2-(5-Methoxy-2-nitrophenoxy)ethyl]dimethylamine → 2-(2-Dimethylaminoethoxy)-4-methoxyphenylamine

Participants

Reaction Steps

A mixture of [2-(5-methoxy-2-nitrophenoxy)ethyl]dimethylamine (1.2 g, 5.0 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (75 mL) was shaken under 50 psi of hydrogen for 24 hours. The mixture was filtered through Celite and evaporated, providing 0.94 g of the product, in 90% yield: 1H NMR (CDCl3) δ 2.34 (s, 6H), 2.75 (t, J=5.8 Hz, 2H), 3.74 (s, 3H), 4.08 (t, J=5.8 Hz, 2H), 6.36 (dd, J=8.4 Hz, J=2.5 Hz, 1H), 6.47 (d, J=2.5 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H).

Provenance & Evidence