hydrogenchloride in methanol 2 h; Heating;

1: 83 percent / pentyl nitrite, trichloroacetic acid / acetic acid / 1.) 2h, 2.) 0 deg C, 3 h 2: 88 percent / H2 / platinum oxide / tetrahydrofuran / 1.5 h / 3040 Torr 3: 79 percent / dimethylformamide / 2 h / Ambient temperature 4: 69 percent / 1.) H2O, acetone, sodium carbonate, 2.) HCl / 1.) water-bath, 0.25 h, 2.) pH=2 5: 83 percent / 0.33 h / 175 - 180 °C 6: 91 percent / H2O, NaOH / methanol / 2 h / water-bath 7: 88 percent / 0.17 h / t > 260 deg C View Scheme

1: 88 percent / H2 / platinum oxide / tetrahydrofuran / 1.5 h / 3040 Torr 2: 79 percent / dimethylformamide / 2 h / Ambient temperature 3: 69 percent / 1.) H2O, acetone, sodium carbonate, 2.) HCl / 1.) water-bath, 0.25 h, 2.) pH=2 4: 83 percent / 0.33 h / 175 - 180 °C 5: 91 percent / H2O, NaOH / methanol / 2 h / water-bath 6: 88 percent / 0.17 h / t > 260 deg C View Scheme

1: 94 percent / ethanol / 3 h / 0 °C 2: 83 percent / pentyl nitrite, trichloroacetic acid / acetic acid / 1.) 2h, 2.) 0 deg C, 3 h 3: 88 percent / H2 / platinum oxide / tetrahydrofuran / 1.5 h / 3040 Torr 4: 79 percent / dimethylformamide / 2 h / Ambient temperature 5: 69 percent / 1.) H2O, acetone, sodium carbonate, 2.) HCl / 1.) water-bath, 0.25 h, 2.) pH=2 6: 83 percent / 0.33 h / 175 - 180 °C 7: 91 percent / H2O, NaOH / methanol / 2 h / water-bath 8: 88 percent / 0.17 h / t > 260 deg C View Scheme

0.166667 h; t > 260 deg C;

1: 83 percent / 0.33 h / 175 - 180 °C 2: 91 percent / H2O, NaOH / methanol / 2 h / water-bath 3: 88 percent / 0.17 h / t > 260 deg C View Scheme

1: 79 percent / dimethylformamide / 2 h / Ambient temperature 2: 69 percent / 1.) H2O, acetone, sodium carbonate, 2.) HCl / 1.) water-bath, 0.25 h, 2.) pH=2 3: 83 percent / 0.33 h / 175 - 180 °C 4: 91 percent / H2O, NaOH / methanol / 2 h / water-bath 5: 88 percent / 0.17 h / t > 260 deg C View Scheme

1: 69 percent / 1.) H2O, acetone, sodium carbonate, 2.) HCl / 1.) water-bath, 0.25 h, 2.) pH=2 2: 83 percent / 0.33 h / 175 - 180 °C 3: 91 percent / H2O, NaOH / methanol / 2 h / water-bath 4: 88 percent / 0.17 h / t > 260 deg C View Scheme

1: 91 percent / H2O, NaOH / methanol / 2 h / water-bath 2: 88 percent / 0.17 h / t > 260 deg C View Scheme