1: 65 percent / ozone, methanolic NaOH / CH2Cl2 / -70 °C 2: 65 percent / quinoline, H2 / Lindlar catalyst / methanol View Scheme

quinoline; hydrogen; ozone; Lindlar's catalyst 1.) MeOH, -60 deg C, 2.) 1 atm; Yield given. Multistep reaction;

1: 1.) O3, 2.) H2, quinoline / 2.) Lindlar catalyst / 1.) MeOH, -60 deg C, 2.) 1 atm 2: 87 percent / 1percent aq. NaOH / diethyl ether / 24 h / Ambient temperature View Scheme