6-(chloromethyl)-3-methoxyquinoline. To a solution of (3-methoxyquinolin-6-yl)methanol (0.17 g, 0.9 mmol) in DMF (10 mL) was added methanesulfonic anhydride (0.4 g, 2 mmol) followed by triethylamine (0.4 ml, 3 mmol). After stirred for 1 h, lithium chloride (0.08 g, 2 mmol) was added. The reaction was continued to stir at rt under N2 for 20 h. The reaction mixture was quenched with water. The resulting mixture was partitioned between EtOAc/sat. NaHCO3 The organic layer was washed with water, brine, dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-026, 12 g SiO2, hex:acetone=90%:10%, Flow=30 mL/min). A peak at 30 min was collected. The solvent was removed in vacuo to afford the desired product as white solid (100 mg). MS (ESI pos. ion) m/z (M+1): 208.4. Calc'd exact mass for C11H10ClNO: 207.66. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.96 (s, 3 H) 4.76 (s, 2 H) 7.37 (d, J=2.78 Hz, 1 H) 7.58 (dd, J=8.62, 1.90 Hz, 1 H) 7.75 (s, 1 H) 8.05 (d, J=8.62 Hz, 1 H) 8.69 (d, J=2.92 Hz, 1 H).
