4-Isopropylaniline → HCID 118699728, compound

Participants

Reaction Steps

To a mixture of 3-(1,4-dihydrobenzo[c]-2,7-naphthyridin-3(2H)-yl)benzoic acid (0.20 mmol, 61 mg) and triethylamine (0.40 mmol, 0.056 mL) in 2.0 mL 1,2-dichloroethane at rt was added propylphosphonic anhydride solution (50 wt % in EtOAc, 0.24 mmol, 0.143 mL). After 10 min at rt, 4-isopropylaniline (0.30 mmol, 0.043 mL) was added and the reaction stirred at rt for 1 hour. Then an additional 0.015 mL 4-isopropylaniline was added, the reaction heated at 60° C. for 5 min, then continued at rt for 3 hours. The reaction was quenched into dilute aqueous Na2CO3 solution, extracted into EtOAc, the EtOAc layer washed with H2O, dilute aqueous Na2CO3 solution, brine, dried with anhydrous Na2SO4 and rotary evaporated. The resulting solid was recrystallized from EtOAc/hexane to give the title compound as an off-white solid (52 mg, 62%).

Provenance & Evidence