Phenethylamine → (2-Nitrophenyl)(2-phenylethyl)amine

Participants

Reaction Steps

1-Chloro-2-nitrobenzene (2 g, 12.7 mmol), phenethylamine (5.1 mL, 40.6 mmol), and N,N-diispropylethylamine (2.8 mL, 15.3 mmol) were dissolved in 1,2-dichloroethane (20 mL) and heated at reflux for 16 hrs. The mixture was concentrated to an oil which was dissolved in EtOAc (200 mL), washed with dilute HCl (3×50 mL), dried over Na2SO4, filtered and concentrated to dryness to give the title compound (3.0g, 97%): 1H NMR (400 MHz, CDCl3) δ 3.0-3.1 (2H, t), 3.5-3.65 (2H, q), 6.65-6.7 (1H, t), 6.85-6.9 (1H, d), 7.25-7.4 (5H, m), 7.45-7.5 (1H, t), 8.15-8.2 (1H, d).

Provenance & Evidence