palladium diacetate in N,N-dimethyl-formamide T=117°C; 3.5 h;

potassium hydrogensulfate

1: LiAlH4 / tetrahydrofuran / Heating 2: Et3N / diethyl ether / -25 °C 3: 2.) AgNO3 / 1.) room temp. 2.) aq. acetonitrile View Scheme

1.1: hydrogenchloride / water / |Reflux 2.1: magnesium / tetrahydrofuran / 15 - 22 °C 2.2: 1 h 3.1: potassium hydroxide / methanol / 1 h View Scheme

1.1: hydrogenchloride / water / 16 h 2.1: magnesium / tetrahydrofuran / 3.5 h / |Inert atmosphere 2.2: 16 h / 25 °C 3.1: potassium hydroxide / methanol / 25 °C 4.1: palladium diacetate; 1,4-di(diphenylphosphino)-butane; potassium carbonate / acetonitrile / 1 h / |Inert atmosphere; |Large scale 4.2: 16 h / 80 °C / |Large scale 5.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / |Inert atmosphere; |Large scale View Scheme

1.1: hydrogenchloride / water / 16 h 2.1: magnesium / tetrahydrofuran / 3.5 h / 10 - 15 °C 2.2: 17.5 h / 25 °C / Cooling with ice 2.3: 5 - 25 °C 3.1: potassium hydroxide / methanol / 5 - 25 °C 3.2: 0.5 h View Scheme

1.1: hydrogenchloride / water / 16 h 2.1: magnesium / tetrahydrofuran / 3.5 h / |Inert atmosphere 2.2: 16 h / 25 °C 3.1: potassium hydroxide / methanol / 25 °C 4.1: palladium diacetate; 1,4-di(diphenylphosphino)-butane; potassium carbonate / acetonitrile / 1 h / |Inert atmosphere; |Large scale 4.2: 16 h / 80 °C / |Large scale 5.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / |Inert atmosphere; |Large scale 6.1: triethylamine / dichloromethane / 0 - 20 °C 7.1: 5 palladium on charcoal; hydrogen / tetrahydrofuran / 50 °C / 2250.23 Torr / |Inert atmosphere; |Sealed tube View Scheme

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane 0.25 h; Ambient temperature; Yield given;

1: 56 percent / Et3N / diethyl ether / -20 °C 2: 40 percent / diethyl ether / Heating View Scheme

1: 77 percent / CaCl2; aq. HCl; Cu/bronze / Cu(I)Cl / 48 h / 20 °C 2: 79 percent / Et3N; H2O; Cu/bronze / Cu(I)Cl / tetrahydrofuran / 4 h / 60 - 70 °C View Scheme