4-Chloroaniline → HCID 59813184, compound

Participants

Reaction Steps

A slurry of 7-(6,7-dimethoxyquinolin-4-yloxy)-2-naphthoic acid (0.54 g, 1.44 mmol) in 10 mL of C2O2Cl2 and 2 drops of DMF was stirred at RT. After 2 h, the solution was concentrated to dryness and placed under high vacuum overnight. A portion of the crude residue (0.075 g, 0.191 mmol) was dissolved in 1 mL of CH2Cl2. To the resulting solution was added Et3N (0.106 mL, 0.76 mmol), 4-chloroaniline (0.036 g, 0.286 mmol) and a catalytic amount of DMAP. The reaction was stirred under a nitrogen atmosphere for 16 h. The reaction was diluted with CH2Cl2, washed with saturated aqueous NaHCO3, and brine. The organic layer was dried (MgSO4), filtered and concentrated. The residue was passed through a medium-pressure silica gel column (solvent gradient: 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH) to afford the desired crude compound. The fractions were concentrated to dryness to afford a solid residue. The residue was triturated with Et2O/Hexanes to afford the desired compound as a pale yellow solid. MS (ESI, pos. ion) m/z: 485.0 (M+1). Mass Calc'd for C28H21ClN2O4: 484.937.

Provenance & Evidence