4-methyl-pyridin-2-ylamine; aniline; benzoic acid; RhCl(PPh3)3 T=130°C; 3 h;

hydrogen; nickel in methanol 6 h; Heating;

nickel dichloride in N,N-dimethyl-formamide T=50°C;

hydrogen bromide in acetic acid 8 h; Heating;

2: 21 percent / N-chlorosuccinimide / benzene / 1.) 0 deg C, 1 h, 2.) room temperature, 4 h 3: 92 percent / Et3N / toluene / 19 h / Ambient temperature 4: 99 percent / toluene-p-sulphonic acid / benzene / 2 h / Heating 5: 99 percent / BuLi / hexane; tetrahydrofuran / 1.) -35 deg C, 30 min, 2.) -78 deg C, 120 min 6: 4M HCl / acetone / 18 h / Heating 7: 75 percent / H2 / Raney nickel / methanol / 6 h / Heating View Scheme

1: 92 percent / Et3N / toluene / 19 h / Ambient temperature 2: 99 percent / toluene-p-sulphonic acid / benzene / 2 h / Heating 3: 99 percent / BuLi / hexane; tetrahydrofuran / 1.) -35 deg C, 30 min, 2.) -78 deg C, 120 min 4: 4M HCl / acetone / 18 h / Heating 5: 75 percent / H2 / Raney nickel / methanol / 6 h / Heating View Scheme

1: 21 percent / N-chlorosuccinimide / benzene / 1.) 0 deg C, 1 h, 2.) room temperature, 4 h 2: 92 percent / Et3N / toluene / 19 h / Ambient temperature 3: 99 percent / toluene-p-sulphonic acid / benzene / 2 h / Heating 4: 99 percent / BuLi / hexane; tetrahydrofuran / 1.) -35 deg C, 30 min, 2.) -78 deg C, 120 min 5: 4M HCl / acetone / 18 h / Heating 6: 75 percent / H2 / Raney nickel / methanol / 6 h / Heating View Scheme

1: 99 percent / toluene-p-sulphonic acid / benzene / 2 h / Heating 2: 99 percent / BuLi / hexane; tetrahydrofuran / 1.) -35 deg C, 30 min, 2.) -78 deg C, 120 min 3: 4M HCl / acetone / 18 h / Heating 4: 75 percent / H2 / Raney nickel / methanol / 6 h / Heating View Scheme

1: 99 percent / BuLi / hexane; tetrahydrofuran / 1.) -35 deg C, 30 min, 2.) -78 deg C, 120 min 2: 4M HCl / acetone / 18 h / Heating 3: 75 percent / H2 / Raney nickel / methanol / 6 h / Heating View Scheme

1: 4M HCl / acetone / 18 h / Heating 2: 75 percent / H2 / Raney nickel / methanol / 6 h / Heating View Scheme