quinoline; Lindlar's catalyst; hydrogen in methanol 60 h; Ambient temperature;

sodium tert-pentoxide in N,N-dimethyl-formamide T=-10°C; 2 h;

sodium in methanol 0.25 h;

1: 65 percent / PPh3, Zn dust / CH2Cl2; dimethylformamide / 48 h / Ambient temperature 2: 95 percent / sodium tert.-pentoxide / dimethylformamide / 2 h / -10 °C View Scheme

1: 51 percent / AgNO3, potassium persulfate / H2O / 3 h / 30 - 40 °C 2: 65 percent / PPh3, Zn dust / CH2Cl2; dimethylformamide / 48 h / Ambient temperature 3: 95 percent / sodium tert.-pentoxide / dimethylformamide / 2 h / -10 °C View Scheme

1: 83 percent / bromine / dimethylformamide / 1.) room temperature, 2 d, 2.) reflux, 5 h 2: 92 percent / sodium / methanol / 0.25 h View Scheme