Hydroquinone → [(S)-1-(4-Bromo-phenyl)-ethyl]-[2-(2-chloro-5-methoxy-4-nitro-phenyl)-ethyl]-amine

Participants

Reaction Steps

A solution of (S)-1-(4-bromophenyl)ethylamine (0.94 g, 4.69 mmol), 1-chloro-4-methoxy-5-nitro-2-vinylbenzene (Example 50C) (0.5 g, 2.34 mmol) and quinol (0.1 g, 0.94 mmol) in n-butanol (6 mL) was heated to reflux for 18 hours. The reaction mixture was concentrated under reduced pressure then the residue partitioned between EtOAc (40 mL) and water (30 mL). The separated aqueous phase was extracted with EtOAc (3×40 mL), and then the combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using 0-1% MeOH in DCM to give the title compound (0.55 g, 57%).

Provenance & Evidence