Potassium Hydroxide → HCID 59536346, compound

Participants

Reaction Steps

To a 100 mL round-bottomed flask was added N-(2-methoxyphenethyl)-4-(trifluoromethyl)benzamide (1.41 g, 4361 μmol, from step 1), toluene (30 mL), phosphorus pentoxide (1077 μL, 17445 μmol, Aldrich). The reaction mixture was stirred at reflux for overnight (ca 18 h). The mixture was cooled down to RT and poured it to ice (ca 100 g). The mixture was neutralized with KOH until pH 12. The mixture was extracted with EtOAc (2×100 mL). The organic extract was washed with saturated NaCl (50 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give 5-methoxy-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline. MS (ESI pos. ion) m/z: 306 (M+1).

Provenance & Evidence