hydrogenchloride; copper(l) chloride; sodium nitrite in water T=0 - 5°C; 2.) 10 min;

1: 45 percent / fuming nitric acid, fuming sulfuric acid / 6 h / 80 - 90 °C 2: 57 percent / sodium / 2 h / Heating 3: 35 percent / sodium bicarbonate, sodium sulfide nonahydrate / H2O / 1 h / Heating 4: 58 percent / 1.) sodium nitrite, 12M HCl; 2.) copper(I) chloride / H2O / 0 - 5 °C / 2.) 10 min View Scheme

1: 35 percent / sodium bicarbonate, sodium sulfide nonahydrate / H2O / 1 h / Heating 2: 58 percent / 1.) sodium nitrite, 12M HCl; 2.) copper(I) chloride / H2O / 0 - 5 °C / 2.) 10 min View Scheme

1: 57 percent / sodium / 2 h / Heating 2: 35 percent / sodium bicarbonate, sodium sulfide nonahydrate / H2O / 1 h / Heating 3: 58 percent / 1.) sodium nitrite, 12M HCl; 2.) copper(I) chloride / H2O / 0 - 5 °C / 2.) 10 min View Scheme

pyrrolidine; hydrogen; palladium on activated charcoal 1.) DMF, reflux, 3 h; 2.) 4 atm; Yield given. Multistep reaction;