1: With sodium carbonate; p-toluenesulfonyl chloride in tetrahydrofuran; water T=20°C; 2 h; 2: With hydrogenchloride in 1,4-dioxane; water 12 h; 3: With sodium hydroxide in water T=0°C; pH=10;

1: T=110°C; 2 h; 2: With platinum(IV) oxide; hydrogen in ethanol T=20°C; P=2585.81 Torr; 72 h;

1: 46 percent / POCl3 / various solvent(s) / 5 h / Heating 2: 82.7 percent / 2 h / 100 °C 3: 74.6 percent / H2 / Raney nickel / ethanol / 24 h / 20 °C / 6080 Torr View Scheme

1: 75 percent / Et3N / 2 h / 80 - 90 °C 2: HCl / diethyl ether 3: xylene / 3 h / 140 °C 4: 30 percent / PdCl2 / nitrobenzene / 2 h / 140 °C 5: 87 percent / Pd/C 5 percent / various solvent(s) / 3 h / Heating 6: 46 percent / POCl3 / various solvent(s) / 5 h / Heating 7: 82.7 percent / 2 h / 100 °C 8: 74.6 percent / H2 / Raney nickel / ethanol / 24 h / 20 °C / 6080 Torr View Scheme

1: 1,4-dimethyl-9H-carbazole; N,N-dimethyl-formamide With trichlorophosphate in chlorobenzene T=131°C; 6.5 h; 2: 2,2-diethoxy-ethanamine T=110°C; 4 h; 3: With platinum(IV) oxide; hydrogen in ethanol T=20°C; P=2585.81 Torr; 72 h;

1: 75 percent / Et3N / 2 h / 80 - 90 °C 2: HCl / diethyl ether 3: xylene / 3 h / 140 °C 4: 30 percent / PdCl2 / nitrobenzene / 2 h / 140 °C 5: 87 percent / Pd/C 5 percent / various solvent(s) / 3 h / Heating 6: 46 percent / POCl3 / various solvent(s) / 5 h / Heating 7: 82.7 percent / 2 h / 100 °C 8: 74.6 percent / H2 / Raney nickel / ethanol / 24 h / 20 °C / 6080 Torr View Scheme

1: 87 percent / Pd/C 5 percent / various solvent(s) / 3 h / Heating 2: 46 percent / POCl3 / various solvent(s) / 5 h / Heating 3: 82.7 percent / 2 h / 100 °C 4: 74.6 percent / H2 / Raney nickel / ethanol / 24 h / 20 °C / 6080 Torr View Scheme

1: HCl / diethyl ether 2: xylene / 3 h / 140 °C 3: 30 percent / PdCl2 / nitrobenzene / 2 h / 140 °C 4: 87 percent / Pd/C 5 percent / various solvent(s) / 3 h / Heating 5: 46 percent / POCl3 / various solvent(s) / 5 h / Heating 6: 82.7 percent / 2 h / 100 °C 7: 74.6 percent / H2 / Raney nickel / ethanol / 24 h / 20 °C / 6080 Torr View Scheme

1: 30 percent / PdCl2 / nitrobenzene / 2 h / 140 °C 2: 87 percent / Pd/C 5 percent / various solvent(s) / 3 h / Heating 3: 46 percent / POCl3 / various solvent(s) / 5 h / Heating 4: 82.7 percent / 2 h / 100 °C 5: 74.6 percent / H2 / Raney nickel / ethanol / 24 h / 20 °C / 6080 Torr View Scheme

1: 47 percent / 5 h / 150 °C 2: 87 percent / Pd/C 5 percent / various solvent(s) / 3 h / Heating 3: 46 percent / POCl3 / various solvent(s) / 5 h / Heating 4: 82.7 percent / 2 h / 100 °C 5: 74.6 percent / H2 / Raney nickel / ethanol / 24 h / 20 °C / 6080 Torr View Scheme