hydrogen; palladium on activated carbon in ethanol P=1551.49 Torr; 1 h;

hydrazine hydrate in ethanol

1: iron; aqueous acetic acid 2: Diazotization View Scheme

1: iron; aqueous acetic acid 2: Diazotization View Scheme

1: 3 h / Reflux 2: ammonium chloride; iron / N,N-dimethyl-formamide; water; acetic acid / 1.5 h / 50 °C View Scheme

potassium carbonate in acetonitrile T=70°C; 18 h;

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 5 h / 20 °C 2: 5 palladium on charcoal; hydrogen / tetrahydrofuran / 3 h / 20 °C / 1500.15 - 2250.23 Torr / |Large scale 3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 4 h / 20 °C / |Large scale 4: N-ethyl-N,N-diisopropylamine; hydrogen; palladium 10 on activated carbon / tetrahydrofuran; isopropyl alcohol / 5.5 h / 40 °C / 1861.76 Torr 5: hydrogenchloride; water / tetrahydrofuran; isopropyl alcohol / 17.5 h / 20 °C 6: hydrogen; palladium 10 on activated carbon / tetrahydrofuran / 7 h / 40 °C / 1861.76 Torr View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2: hydrogen / palladium 10 on activated carbon / ethanol / 2 h View Scheme

1: potassium carbonate / dimethyl sulfoxide / 20 °C 2: iron; ammonium chloride / tetrahydrofuran; water / 3 h / |Reflux 3: trifluoroacetic acid / Sec-butyl alcohol / 3 h / |Reflux 4: iron; ammonium chloride / tetrahydrofuran; water / 3 h / |Reflux 5: triethylamine / dichloromethane / 1 h / 0 °C View Scheme

potassium carbonate in N,N-dimethyl-formamide T=70°C; 12 h;