1: thionyl chloride (SOCl2) / 1 h / Heating 2: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 3: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 4: p-toluenesulfonic acid / toluene / 3 h / Heating 5: 32 percent / AgNO2, NaNO2, I2 / acetonitrile / 48 h / Ambient temperature 6: hydrazine monohydrate / Pd/C / tetrahydrofuran / 1 h / 0 °C View Scheme

1: thionyl chloride (SOCl2) / 1 h / Heating 2: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 3: 16 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 4: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 5: p-toluenesulfonic acid / toluene / 3 h / Heating 6: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating View Scheme

1: thionyl chloride (SOCl2) / 1 h / Heating 2: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 3: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 4: p-toluenesulfonic acid / toluene / 3 h / Heating 5: 32 percent / AgNO2, NaNO2, I2 / acetonitrile / 48 h / Ambient temperature View Scheme

1: thionyl chloride (SOCl2) / 1 h / Heating 2: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 3: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 4: p-toluenesulfonic acid / toluene / 3 h / Heating View Scheme

1: thionyl chloride (SOCl2) / 1 h / Heating 2: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 3: 25 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 4: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 5: p-toluenesulfonic acid / toluene / 3 h / Heating 6: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating View Scheme

1: thionyl chloride (SOCl2) / 1 h / Heating 2: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 3: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 4: p-toluenesulfonic acid / toluene / 3 h / Heating 5: 32 percent / AgNO2, NaNO2, I2 / acetonitrile / 48 h / Ambient temperature 6: 94 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

1: thionyl chloride (SOCl2) / 1 h / Heating 2: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 3: 16 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 4: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 5: p-toluenesulfonic acid / toluene / 3 h / Heating 6: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 7: 95 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

sodium hydroxide in tetrahydrofuran T=80°C; 2 h;

1: H2 / 10percent Pd/C / ethanol / 12 h / 2275.5 Torr 2: 2N NaOH View Scheme

sulfuric acid in water; acetone