[2-(3-Isopropoxy-4-nitrophenoxy)ethyl]dimethylamine → 4-(2-Dimethylaminoethoxy)-2-isopropoxyphenylamine

Participants

Reaction Steps

A mixture of [2-(3-isopropoxy-4-nitrophenoxy)ethyl]dimethylamine (2.0 g, 7.5 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (70 mL) was shaken under 50 psi of hydrogen for 24 hours. The mixture was filtered through Celite and evaporated, providing 1.7 g of the product as a light gold oil, in 98% yield; 1H NMR (CDCl3) δ 1.34 (d, J=6.0 Hz, 6H), 2.32 (s, 6H), 2.68 (t, J=5.8 Hz, 2H), 3.48 (br, 2H), 3.98 (t, J=5.8 Hz, 2H), 4.48 (septet, J=6.0 Hz, 1H), 6.35 (dd, J=8.4 Hz, J=2.5 Hz, 1H), 6.50 (d, J=2.5 Hz, 1H), 6.63 (d, J=8.4 Hz, 1H).

Provenance & Evidence