Water → HCID 21939647, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-[2-(4-nitrobenzyl)phenyl]acetamide (6.80 g, 25.2 mmol) in EtOAc (700 mL) was treated with Pd (10% on C, 0.53 g, 0.5 mmol). The mixture was stirred under a H2 atmosphere for 5 h. The reaction mixture was filtered through Celite, before being concentrated to yield N-[2-(4-aminobenzyl)phenyl]acetamide (6.00 g, 99%): δH ((CD3)2SO)=2.00 (s, 3H), 3.75 (s, 2H), 4.80 (s, 2H), 6.45 (d, 2H), 6.80 (d, 2H), 7.00–7.15 (m, 3H), 7.35 (d, 1H), 9.20 (s, 1H). A PhMe (75 mL) suspension of this aniline (5.00 g, 20.8 mmol) was treated with a solution of CF3COCH2CO2Et (3.83 g, 20.8 mmol) in PhMe (50 mL), before being heated under reflux for 1.5 h. The PhMe was evaporated off under reduced pressure, then the residue was dissolved in EtOAc (400 mL), before being washed with 0.2 M HCl (50 mL) & brine (50 mL). After drying (MgSO4), the EtOAc solution was filtered & concentrated to give a foam that was dissolved in H2SO4 (40 mL). The mixture was heated at 90° C. for 1.5 h, before being cooled & poured onto crushed ice. H2O was added to adjust the volume to 400 mL, then the off-white precipitate produced was collected by filtration & air-dried. The precipitate was treated with AcOH (8 mL) & 12 M HCl (40 mL), & the resulting suspension was heated under reflux. The solid gradually dissolved & heating was stopped after 4 h. The cooled reaction mixture was poured onto crushed ice (50 g), then H2O (200 mL) was added. The aqueous phase was basicified with solid NaOH, then the mixture was extracted with EtOAc (200 mL). The EtOAc layer was dried (MgSO4), filtered, & concentrated to provide the title compound (3.01 g, 45%): δH ((CD3)2SO)=3.85 (s, 2H), 4.85 (s, 2H), 6.50 (t, 1H), 6.60 (d, 1H), 6.85 (d, 1H), 6.90–7.00 (m, 2H), 7.35 (d, 1H), 7.50 (d, 1H), 7.55 (s, 1H); m/z (ES+)=360.3

Provenance & Evidence