1,2-diethyl-3-nitrobenzene → 3,4-Diethylaniline

Participants

Reaction Steps

A mixture of 1,2-diethyl-4-nitrobenzene (16) and 1,2-diethyl-3-nitrobenzene (17) (1.4 g, 7.82 mmol) was dissolved in ethyl acetate (20 mL). To this solution was added 10% Pd--C (350 mg, 20%; Aldrich). The mixture was agitated at room temperature under a pressure of 35 psi (H2) for 10 h. The catalyst was removed through a column of Celite (5 g) and washed with ethyl acetate (3×15 mL). The filtrates were combined and evaporated in vacuo to give a residue, which was separated by preparative TLC (Hexanes:EtOAc=8:2), giving 3,4-diethylaniline (19) (0.822 g, 71%) as a pale yellow oil (Rf =0.7) and 2,3-diethylaniline (20) (0.219 g, 19%) as a brown oil (Rf =0.6). 1H NMR (CDCl3, 300 MHz): δ(19): 1.184 (t, 6H, J=7 Hz), 2.573 (q, 4H, J=7 Hz), 3.456 (br, s, 2H) 6.513 (m, 2H), 6.970 (d, 1H, J=7.8 Hz). (20): 1.215 (t, 6H, J=7 Hz), 2.617 (q, 4H, J=7 Hz), 6.570 (d, 1H, J=7.5 Hz), 6.650 (d, 1H, J=7.5 Hz), 6.973 (m, 1H).

Provenance & Evidence