sodium tetrahydroborate in ethanol 1 h; Ambient temperature;

1: 63 percent / conc. H2SO4, conc. HNO3 / 0.33 h / 15 °C 2: 1.) NaOEt / 1.) EtOH, 5 deg C, 20 min, 2.) EtOH, reflux, 3 h 3: 100 percent / aq. NaOH / ethanol / 3 h / Heating 4: 89 percent / Cu, quinoline / 3 h / 190 °C 5: 1.) pyrrolidine, 2.) aq. HCl / 1.) DMF, 150 deg C, 3 h, 2.) toluene, reflux, 30 min 6: 98 percent / NaBH4 / ethanol / 1 h / Ambient temperature View Scheme

1: 1.) pyrrolidine, 2.) aq. HCl / 1.) DMF, 150 deg C, 3 h, 2.) toluene, reflux, 30 min 2: 98 percent / NaBH4 / ethanol / 1 h / Ambient temperature View Scheme

1: 1.) NaOEt / 1.) EtOH, 5 deg C, 20 min, 2.) EtOH, reflux, 3 h 2: 100 percent / aq. NaOH / ethanol / 3 h / Heating 3: 89 percent / Cu, quinoline / 3 h / 190 °C 4: 1.) pyrrolidine, 2.) aq. HCl / 1.) DMF, 150 deg C, 3 h, 2.) toluene, reflux, 30 min 5: 98 percent / NaBH4 / ethanol / 1 h / Ambient temperature View Scheme

1: 89 percent / Cu, quinoline / 3 h / 190 °C 2: 1.) pyrrolidine, 2.) aq. HCl / 1.) DMF, 150 deg C, 3 h, 2.) toluene, reflux, 30 min 3: 98 percent / NaBH4 / ethanol / 1 h / Ambient temperature View Scheme

1: 100 percent / aq. NaOH / ethanol / 3 h / Heating 2: 89 percent / Cu, quinoline / 3 h / 190 °C 3: 1.) pyrrolidine, 2.) aq. HCl / 1.) DMF, 150 deg C, 3 h, 2.) toluene, reflux, 30 min 4: 98 percent / NaBH4 / ethanol / 1 h / Ambient temperature View Scheme