ammonia in methanol T=140 - 175°C; P=45600 Torr; 116 h;

ammonia T=160 - 170°C; 18 h;

ammonia T=160 - 170°C; 18 h;

1: 56 percent / H2, NaOAc / 5percent Pd/C / dimethylformamide / 1 h / 2280 Torr 2: 73 percent / LiBH4 / tetrahydrofuran 3: 69 percent / NH3 / methanol / 116 h / 140 - 175 °C / 45600 Torr View Scheme

1: 89 percent / Na / 2 h / Ambient temperature 2: 56 percent / H2, NaOAc / 5percent Pd/C / dimethylformamide / 1 h / 2280 Torr 3: 73 percent / LiBH4 / tetrahydrofuran 4: 69 percent / NH3 / methanol / 116 h / 140 - 175 °C / 45600 Torr View Scheme

1: 45 percent / POCl3, N,N-diethylaniline / 12 h / Heating 2: 89 percent / Na / 2 h / Ambient temperature 3: 56 percent / H2, NaOAc / 5percent Pd/C / dimethylformamide / 1 h / 2280 Torr 4: 73 percent / LiBH4 / tetrahydrofuran 5: 69 percent / NH3 / methanol / 116 h / 140 - 175 °C / 45600 Torr View Scheme

1: 44 percent / diphenyl ether; biphenyl / 0.03 h / Heating 2: 45 percent / POCl3, N,N-diethylaniline / 12 h / Heating 3: 89 percent / Na / 2 h / Ambient temperature 4: 56 percent / H2, NaOAc / 5percent Pd/C / dimethylformamide / 1 h / 2280 Torr 5: 73 percent / LiBH4 / tetrahydrofuran 6: 69 percent / NH3 / methanol / 116 h / 140 - 175 °C / 45600 Torr View Scheme

1: 73 percent / LiBH4 / tetrahydrofuran 2: 69 percent / NH3 / methanol / 116 h / 140 - 175 °C / 45600 Torr View Scheme

1: 62 percent / POCl3, (C2H5)3N / 8 h / Heating 2: 84 percent / liquid NH3 / 18 h / 160 - 170 °C View Scheme

1: 85 percent / acetic acid / 0.5 h / Heating 2: 62 percent / POCl3, (C2H5)3N / 8 h / Heating 3: 84 percent / liquid NH3 / 18 h / 160 - 170 °C View Scheme