sodium sulfide; ethanol

1: potassium carbonate / N,N-dimethyl-formamide / 72 h / 20 °C 2: hydrogen; 50 Pd/C / methanol; tetrahydrofuran / 10 h / 32 °C View Scheme

1: 96 percent / methanol / Heating 2: 100 percent / H2 / Pd/C / ethanol; ethyl acetate / 2068.6 Torr 3: 1.) NaNO2, HCl, 2.) H3PO2 / 1.) H2O, 15 min, 2.) H2O, 4 deg C, overnight, 20 deg C, 2 h View Scheme

1: NH3 / ethanol 2: (i) H2, PtO2, (ii) /BRN= 1209246/ 3: aq. HCl View Scheme

sodium methylate in methanol

1.1: 92 percent / methanol 2.1: 91 percent / H2 / Pd/C / ethanol 3.1: 68 percent / HCl; NaNO2; NaI / H2O / 16 h / 0 - 22 °C 4.1: 96 percent / acetonitrile / 0.01 h / microwave irradiation 5.1: 72 percent / BBr3 / CH2Cl2 / 40 °C 6.1: 82 percent / 220 °C 7.1: 65 percent / NaH / dimethylformamide 8.1: iPrMgCl / tetrahydrofuran / 2 h / -20 °C 8.2: tetrahydrofuran / 16 h / -20 - 22 °C 8.3: 72 percent / TFA / CH2Cl2 / 2 h / 22 °C View Scheme

1: NH3 / ethanol 2: (i) H2, PtO2, (ii) /BRN= 1209246/ View Scheme

1: 92 percent / methanol 2: 91 percent / H2 / Pd/C / ethanol 3: 68 percent / HCl; NaNO2; NaI / H2O / 16 h / 0 - 22 °C 4: 96 percent / acetonitrile / 0.01 h / microwave irradiation 5: 72 percent / BBr3 / CH2Cl2 / 40 °C View Scheme

1: ethanol; sodium sulfide 2: iron; aq.-ethanolic NH4Cl View Scheme