triphenylphosphine in tetrahydrofuran T=20°C; Staudinger Azide Reduction; 0.333333 h; Inert atmosphere;

tin(ll) chloride in toluene 4 h; Heating;

zinc(II) chloride in N,N-dimethyl-formamide Friedlaender synthesis; 1 h; Reflux;

1: sulfuric acid / 1,2,3,4-tetrahydro-naphthalene / 1 h / 150 - 210 °C / |Inert atmosphere 2: trichlorophosphate / water / 0.5 h / |Reflux; |Inert atmosphere 3: sodium azide / N,N-dimethyl-formamide / 2 h / 100 °C / |Inert atmosphere 4: triphenylphosphine / tetrahydrofuran / 0.33 h / 20 °C / |Inert atmosphere View Scheme

1: trichlorophosphate / water / 0.5 h / |Reflux; |Inert atmosphere 2: sodium azide / N,N-dimethyl-formamide / 2 h / 100 °C / |Inert atmosphere 3: triphenylphosphine / tetrahydrofuran / 0.33 h / 20 °C / |Inert atmosphere View Scheme

1: sodium azide / N,N-dimethyl-formamide / 2 h / 100 °C / |Inert atmosphere 2: triphenylphosphine / tetrahydrofuran / 0.33 h / 20 °C / |Inert atmosphere View Scheme

1: pyridine / 1 h / 60 °C / |Inert atmosphere 2: ammonium formate; 5 palladium on charcoal / methanol / 20 h / 20 °C / |Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C / |Inert atmosphere 4: dichloromethane View Scheme

potassium hydroxide; nickel monoaluminide in methanol; water T=60°C; 2 h;