hydrogenchloride 24 h; Heating;

hydrogenchloride 18 h; Heating;

1: 1.) NaH / 1.) DMF, -10 deg C, 30 min, 2.) DMF, -15 deg C, 30 min 2: 29 percent / H2O / 5 h / 150 °C 3: 58 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 4: 96 percent / 2N aq. HCl / methanol / 2 h / Heating 5: SOCl2 / CHCl3 / 1 h / Heating 6: dimethylformamide / 1 h / Ambient temperature 7: 65 percent / piperidine / ethanol / 18 h / Heating 8: 56 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature 9: 72 percent / 4N aq. HCl / 18 h / Heating View Scheme

1: 73 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 2: 1.) NaH / 1.) DMF, -10 deg C, 30 min, 2.) DMF, -15 deg C, 30 min 3: 29 percent / H2O / 5 h / 150 °C 4: 58 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 5: 96 percent / 2N aq. HCl / methanol / 2 h / Heating 6: SOCl2 / CHCl3 / 1 h / Heating 7: dimethylformamide / 1 h / Ambient temperature 8: 65 percent / piperidine / ethanol / 18 h / Heating 9: 56 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature 10: 72 percent / 4N aq. HCl / 18 h / Heating View Scheme

1: 29 percent / H2O / 5 h / 150 °C 2: 58 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 3: 96 percent / 2N aq. HCl / methanol / 2 h / Heating 4: SOCl2 / CHCl3 / 1 h / Heating 5: dimethylformamide / 1 h / Ambient temperature 6: 65 percent / piperidine / ethanol / 18 h / Heating 7: 56 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature 8: 72 percent / 4N aq. HCl / 18 h / Heating View Scheme

1: 58 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 2: 96 percent / 2N aq. HCl / methanol / 2 h / Heating 3: SOCl2 / CHCl3 / 1 h / Heating 4: dimethylformamide / 1 h / Ambient temperature 5: 65 percent / piperidine / ethanol / 18 h / Heating 6: 56 percent / NaBH4, 1.0N aq. NaOH, CoCl2*6H2O, 2,2'-dipyridyl / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature 7: 72 percent / 4N aq. HCl / 18 h / Heating View Scheme

1: 85 percent / SOCl2 / CHCl3 / 0.5 h / Heating 2: 98 percent / dimethylformamide / 2 h / 60 °C 3: H2 / 5percent Pd/C / ethyl acetate / 760 Torr 4: 1.) aq. HBr, NaNO2, 2.) Cu2O / 1.) acetone, 5 deg C, 2.) acetone 5: 38 percent / NaOAc / ethanol / 5 h / Heating 6: 79 percent / 4N HCl / 24 h / Heating View Scheme

1: 98 percent / dimethylformamide / 2 h / 60 °C 2: H2 / 5percent Pd/C / ethyl acetate / 760 Torr 3: 1.) aq. HBr, NaNO2, 2.) Cu2O / 1.) acetone, 5 deg C, 2.) acetone 4: 38 percent / NaOAc / ethanol / 5 h / Heating 5: 79 percent / 4N HCl / 24 h / Heating View Scheme

1: H2 / 5percent Pd/C / ethyl acetate / 760 Torr 2: 1.) aq. HBr, NaNO2, 2.) Cu2O / 1.) acetone, 5 deg C, 2.) acetone 3: 38 percent / NaOAc / ethanol / 5 h / Heating 4: 79 percent / 4N HCl / 24 h / Heating View Scheme

1: 88 percent / 2N HCl / methanol / 2 h / Heating 2: 85 percent / SOCl2 / CHCl3 / 0.5 h / Heating 3: 98 percent / dimethylformamide / 2 h / 60 °C 4: H2 / 5percent Pd/C / ethyl acetate / 760 Torr 5: 1.) aq. HBr, NaNO2, 2.) Cu2O / 1.) acetone, 5 deg C, 2.) acetone 6: 38 percent / NaOAc / ethanol / 5 h / Heating 7: 79 percent / 4N HCl / 24 h / Heating View Scheme