1: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 2: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 3: 95 percent / HNO3 / 0.02 h / 60 °C 4: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 5: 78 percent / CH3ONa / methanol / 1 h 6: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 3: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 4: 95 percent / HNO3 / 0.02 h / 60 °C 5: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 6: 78 percent / CH3ONa / methanol / 1 h 7: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme

1: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 2: 78 percent / CH3ONa / methanol / 1 h 3: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme

1: 95 percent / HNO3 / 0.02 h / 60 °C 2: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 3: 78 percent / CH3ONa / methanol / 1 h 4: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme

1: 78 percent / CH3ONa / methanol / 1 h 2: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme

1: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 2: 95 percent / HNO3 / 0.02 h / 60 °C 3: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 4: 78 percent / CH3ONa / methanol / 1 h 5: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme

hydrogenchloride; ammonia 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d; Yield given. Multistep reaction;