hydrogen; platinum(IV) oxide in methanol; ammonium hydroxide

hydrogenchloride in dichloromethane T=0°C; 1 h;

ammonia 48 h; Ambient temperature;

1: 75 percent / KOH, Bu4NHSO4 / tetrahydrofuran / 20 °C 2: 17 percent / liq. NH3 / 48 h / 20 °C / sealed tube View Scheme

ammonia T=20°C; 144 h; sealed tube;

1: 80 percent / diethyl ether / 1 h / Ambient temperature 2: 88 percent / 25percent aq. sodium sulfite, 10percent aq. KOH / diethyl ether; CHCl3 / 1 h 3: 75 percent / tetrabutylammonium hydrogen sulfate, KOH / tetrahydrofuran / 5 h / Ambient temperature 4: 18 percent / NH3 liquid / 48 h / Ambient temperature View Scheme

1: 88 percent / 25percent aq. sodium sulfite, 10percent aq. KOH / diethyl ether; CHCl3 / 1 h 2: 75 percent / tetrabutylammonium hydrogen sulfate, KOH / tetrahydrofuran / 5 h / Ambient temperature 3: 18 percent / NH3 liquid / 48 h / Ambient temperature View Scheme

1.1: N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 0.5 h / 0 °C 1.2: CH2Cl2 / 10 h / 20 °C 2.1: 62 percent / NaH / dimethylformamide; CH2Cl2 / 12 h / 20 °C 3.1: 69 percent / HCl gas / CH2Cl2 / 1 h / 0 °C View Scheme

1: 62 percent / NaH / dimethylformamide; CH2Cl2 / 12 h / 20 °C 2: 69 percent / HCl gas / CH2Cl2 / 1 h / 0 °C View Scheme

sodium hydroxide in dichloromethane T=55°C; 12 h;