quinoline; hydrogen; Lindlar's catalyst in methanol

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

1: 70 percent / PBr3, pyridine / 2 h / Ambient temperature 2: 57 percent / NaNO2 / dimethylformamide / 5 h / Ambient temperature 3: 75 percent / Amberlyst A21 / diethyl ether / 24 h / Ambient temperature 4: 1.) MeONa, 2.) conc. H2SO4 / 1.) MeOh, 2.) -35 deg C, 10 min View Scheme

1: 57 percent / NaNO2 / dimethylformamide / 5 h / Ambient temperature 2: 75 percent / Amberlyst A21 / diethyl ether / 24 h / Ambient temperature 3: 1.) MeONa, 2.) conc. H2SO4 / 1.) MeOh, 2.) -35 deg C, 10 min View Scheme

1: 75 percent / Amberlyst A21 / diethyl ether / 24 h / Ambient temperature 2: 1.) MeONa, 2.) conc. H2SO4 / 1.) MeOh, 2.) -35 deg C, 10 min View Scheme

sulfuric acid; sodium methylate 1.) MeOh, 2.) -35 deg C, 10 min; Yield given. Multistep reaction;

1.) N-methyl-2-pyrrolidone, RT, 1 h, 2.) N-methyl-2-pyrrolidone, 20 h; Yield given. Multistep reaction;