N-Ethylaniline → HCID 67045409, compound

Participants

Reaction Conditions

Reaction Steps

1-Bromo 3-nitrobenzene (500 mg, 2.5 mmol) and N-ethylaniline (375 μL, 3.0 mmol) were dissolved in toluene (15 ml) and sodium butoxide (193 mg, 2.0 mmol), Xantphos (143 mg, 0.25 mmol) and tris (dibenzylideneacetone) dipalladium (57 mg, 0.06 mmol) were added. The reaction mixture was stirred at 110° C. for 16 hours. The mixture was filtered through celite and the filtrate was concentrated to give crude product, which was purified by column chromatography (9:1 hexanes-ethyl acetate) to give N-ethyl-3-nitro-N-phenylaniline as colorless oil (400 mg, 1.65 mmol, 67% yield). 1H NMR (400 MHz, CDCl3): 6.99-7.59 (m, 8H), 6.58-6.69 (m, 1H), 3.79 (q, 2H), 1.25 (t, 3H); MS (EI) for C14H14N2O2: 242 (MH+).

Provenance & Evidence