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

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

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

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

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

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

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

1: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 2: 25 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 3: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 4: p-toluenesulfonic acid / toluene / 3 h / Heating 5: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 6: 96 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

aluminium trichloride in dichloromethane T=0°C; 0.333333 h; Yield given;

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