1: xylene 2: N2H4+H2O; ethanol View Scheme

1: SnCl2; concentrated aqueous HCl 3: xylene 4: N2H4+H2O; ethanol View Scheme

1.1: 100 percent / Et3N / CH2Cl2 / 1 h / 20 °C 2.1: POCl3 / 1 h / 0 °C 2.2: 99 percent / 3 h / 25 °C 3.1: 100 percent / pyridine / 12 h / 25 °C 4.1: 12.8 mg / MnO2; pyridine / benzene / 2 h / 65 °C 5.1: 67 percent / Dess-Martin periodinane; H2O / CH2Cl2 / 12 h / 25 °C 6.1: 95 percent / NH3 / tetrahydrofuran / 48 h / -78 - 25 °C View Scheme

4-(N,N-dimethlyamino)pyridine in pyridine T=0 - 20°C;