hydrogenchloride; sodium in tetrahydrofuran 53 h; Ambient temperature;

formic acid; nickel in water 6 h; Heating;

1: 92 percent / H2 / 10percent Pd/C / methanol 2: 78 percent / Br2, dioxane / diethyl ether / 0.5 h 3: K, NH3(liquid), Fe(NO3)3 / 3 h 4: 1.) HNO2, 2.) Cu2(CN)2, NaCN / 1.) 0 deg C, 2.) a) H2O, toluene, 0 deg C, 30 min, b) 60 deg C, 1 h 5: 70 percent / 90percent formic acid / Raney Ni / H2O / 6 h / Heating View Scheme

1: 78 percent / Br2, dioxane / diethyl ether / 0.5 h 2: K, NH3(liquid), Fe(NO3)3 / 3 h 3: 1.) HNO2, 2.) Cu2(CN)2, NaCN / 1.) 0 deg C, 2.) a) H2O, toluene, 0 deg C, 30 min, b) 60 deg C, 1 h 4: 70 percent / 90percent formic acid / Raney Ni / H2O / 6 h / Heating View Scheme

1: 1.) HNO2, 2.) Cu2(CN)2, NaCN / 1.) 0 deg C, 2.) a) H2O, toluene, 0 deg C, 30 min, b) 60 deg C, 1 h 2: 70 percent / 90percent formic acid / Raney Ni / H2O / 6 h / Heating View Scheme

1: K, NH3(liquid), Fe(NO3)3 / 3 h 2: 1.) HNO2, 2.) Cu2(CN)2, NaCN / 1.) 0 deg C, 2.) a) H2O, toluene, 0 deg C, 30 min, b) 60 deg C, 1 h 3: 70 percent / 90percent formic acid / Raney Ni / H2O / 6 h / Heating View Scheme

1: 83 percent / NH4Cl / methanol / 3 h / Heating 2: 75 percent / 1) Na, 2) 1N HCl / tetrahydrofuran / 53 h / Ambient temperature View Scheme

1.1: Na / tetrahydrofuran / 24 h / 20 °C 1.2: 12 h / 20 °C 2.1: 1.1 g / HCl; water / tetrahydrofuran / 5 h / 20 °C View Scheme

1: t-BuOK / 2-methyl-propan-2-ol; dimethylsulfoxide / 1.5 h / 55 - 60 °C 2: NaOMe / ethanol / 24 h / Heating View Scheme