1: 1.) 2N NaOH, 2.) 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / 1.) ice water, 2.) THF, overnight, room temp. 2: 1.) HBr, 2.) Et3N / 1.) AcOH. 20 min, 2.) EtOH 3: 89 percent / acetic acid / 2 h 4: 65 percent / NaHCO3 / H2O / 3 h / Ambient temperature View Scheme

hydrogenchloride; hydrogen; palladium 1.) ether, 20 deg C; 2.) methanol, acetic acid, 5 h, 20 deg C; Yield given. Multistep reaction;