1: 4-(N,N-dimethlyamino)pyridine; triethylamine / toluene / 1 h / 20 °C 2: 88 °C 3: hydrogen / palladium 10 on activated carbon / methanol / 47 h / 50 °C / 3750.38 Torr View Scheme

1.1: 5 palladium on charcoal; hydrogen / methanol / 12 h / 20 °C 2.1: methanol / 1 h / 20 °C 3.1: triethylsilane / dichloromethane / 20 °C 3.2: -78 - -75 °C 4.1: hydrogenchloride / methanol / 2 h / 50 - 55 °C 4.2: pH 10.5 - 11 5.1: triethylamine / dichloromethane / 3 h / 20 °C 6.1: triethylamine; 2-hydroxy-pyridine / 36 h / 60 - 65 °C View Scheme

1.1: 5 palladium on charcoal; hydrogen / methanol / 12 h / 20 °C 2.1: methanol / 1 h / 20 °C 3.1: triethylsilane / dichloromethane / 20 °C 3.2: -78 - -75 °C 4.1: hydrogenchloride / methanol / 2 h / 50 - 55 °C 4.2: pH 10.5 - 11 5.1: triethylamine / dichloromethane / 3 h / 20 °C View Scheme