1: 86 percent / butan-1-ol / 4 h / Heating 2: H2 / Raney Ni / dimethylformamide; aq. NH3 / 2 h / 25 °C / 2280 Torr 3: 80 percent / HCOOH / 3 h / Heating 4: 92 percent / aq. HCl / ethanol / 1.5 h / Heating 6: 80 percent / isoamyl nitrite / ethanol; HCl / 1.) 0 deg C, 30 min, 2.) 25 deg C, 16 h 7: 76 percent / acetic anhydride / 1 h / 140 °C 8: SnCl2*2H2O, 12N HCl / H2O / 1.) 0 deg C, 2 h, 2.) 25 deg C, 16 h 9: KOH / H2O; ethanol / 2 h / Heating 10: 85 percent / Na / ethanol / 3 h / Heating 11: 80 percent / Et4N(1+)Cl(1-), PhNEt2,POCl3 / acetonitrile / 4 h / 100 °C 12: 53 percent / Na / NH3 / 2.5 h / -75 °C 13: 11 percent / 810 - 850 °C / 0 Torr View Scheme

1: H2 / Raney Ni / dimethylformamide; aq. NH3 / 2 h / 25 °C / 2280 Torr 2: 80 percent / HCOOH / 3 h / Heating 3: 92 percent / aq. HCl / ethanol / 1.5 h / Heating 5: 80 percent / isoamyl nitrite / ethanol; HCl / 1.) 0 deg C, 30 min, 2.) 25 deg C, 16 h 6: 76 percent / acetic anhydride / 1 h / 140 °C 7: SnCl2*2H2O, 12N HCl / H2O / 1.) 0 deg C, 2 h, 2.) 25 deg C, 16 h 8: KOH / H2O; ethanol / 2 h / Heating 9: 85 percent / Na / ethanol / 3 h / Heating 10: 80 percent / Et4N(1+)Cl(1-), PhNEt2,POCl3 / acetonitrile / 4 h / 100 °C 11: 53 percent / Na / NH3 / 2.5 h / -75 °C 12: 11 percent / 810 - 850 °C / 0 Torr View Scheme

T=810 - 850°C; P=0.001 Torr;

2: 80 percent / isoamyl nitrite / ethanol; HCl / 1.) 0 deg C, 30 min, 2.) 25 deg C, 16 h 3: 76 percent / acetic anhydride / 1 h / 140 °C 4: SnCl2*2H2O, 12N HCl / H2O / 1.) 0 deg C, 2 h, 2.) 25 deg C, 16 h 5: KOH / H2O; ethanol / 2 h / Heating 6: 85 percent / Na / ethanol / 3 h / Heating 7: 80 percent / Et4N(1+)Cl(1-), PhNEt2,POCl3 / acetonitrile / 4 h / 100 °C 8: 53 percent / Na / NH3 / 2.5 h / -75 °C 9: 11 percent / 810 - 850 °C / 0 Torr View Scheme

1: 80 percent / HCOOH / 3 h / Heating 2: 92 percent / aq. HCl / ethanol / 1.5 h / Heating 4: 80 percent / isoamyl nitrite / ethanol; HCl / 1.) 0 deg C, 30 min, 2.) 25 deg C, 16 h 5: 76 percent / acetic anhydride / 1 h / 140 °C 6: SnCl2*2H2O, 12N HCl / H2O / 1.) 0 deg C, 2 h, 2.) 25 deg C, 16 h 7: KOH / H2O; ethanol / 2 h / Heating 8: 85 percent / Na / ethanol / 3 h / Heating 9: 80 percent / Et4N(1+)Cl(1-), PhNEt2,POCl3 / acetonitrile / 4 h / 100 °C 10: 53 percent / Na / NH3 / 2.5 h / -75 °C 11: 11 percent / 810 - 850 °C / 0 Torr View Scheme

1: 92 percent / aq. HCl / ethanol / 1.5 h / Heating 3: 80 percent / isoamyl nitrite / ethanol; HCl / 1.) 0 deg C, 30 min, 2.) 25 deg C, 16 h 4: 76 percent / acetic anhydride / 1 h / 140 °C 5: SnCl2*2H2O, 12N HCl / H2O / 1.) 0 deg C, 2 h, 2.) 25 deg C, 16 h 6: KOH / H2O; ethanol / 2 h / Heating 7: 85 percent / Na / ethanol / 3 h / Heating 8: 80 percent / Et4N(1+)Cl(1-), PhNEt2,POCl3 / acetonitrile / 4 h / 100 °C 9: 53 percent / Na / NH3 / 2.5 h / -75 °C 10: 11 percent / 810 - 850 °C / 0 Torr View Scheme

1: KOH / H2O; ethanol / 2 h / Heating 2: 85 percent / Na / ethanol / 3 h / Heating 3: 80 percent / Et4N(1+)Cl(1-), PhNEt2,POCl3 / acetonitrile / 4 h / 100 °C 4: 53 percent / Na / NH3 / 2.5 h / -75 °C 5: 11 percent / 810 - 850 °C / 0 Torr View Scheme

1: 85 percent / Na / ethanol / 3 h / Heating 2: 80 percent / Et4N(1+)Cl(1-), PhNEt2,POCl3 / acetonitrile / 4 h / 100 °C 3: 53 percent / Na / NH3 / 2.5 h / -75 °C 4: 11 percent / 810 - 850 °C / 0 Torr View Scheme

1: 80 percent / isoamyl nitrite / ethanol; HCl / 1.) 0 deg C, 30 min, 2.) 25 deg C, 16 h 2: 76 percent / acetic anhydride / 1 h / 140 °C 3: SnCl2*2H2O, 12N HCl / H2O / 1.) 0 deg C, 2 h, 2.) 25 deg C, 16 h 4: KOH / H2O; ethanol / 2 h / Heating 5: 85 percent / Na / ethanol / 3 h / Heating 6: 80 percent / Et4N(1+)Cl(1-), PhNEt2,POCl3 / acetonitrile / 4 h / 100 °C 7: 53 percent / Na / NH3 / 2.5 h / -75 °C 8: 11 percent / 810 - 850 °C / 0 Torr View Scheme

1: 80 percent / Et4N(1+)Cl(1-), PhNEt2,POCl3 / acetonitrile / 4 h / 100 °C 2: 53 percent / Na / NH3 / 2.5 h / -75 °C 3: 11 percent / 810 - 850 °C / 0 Torr View Scheme