1.1: 6 percent / sodium / 2-methyl-propan-2-ol; toluene / 22 h / Heating 2.1: 100 percent / pyridine; 4-(dimethylamino)pyridine / 20 °C 3.1: 79 percent / lithium triethylborohydride / dimethylsulfoxide / 1 h / 65 °C 4.1: 93 percent / H2 / Pd/C / CH2Cl2; methanol / 20 °C 5.1: pyridine / 5 h / Heating 6.1: 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C 7.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 8.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 9.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 10.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 10.2: 77 percent / KOH / 2 h / Heating View Scheme

With  pyridinium chlorochromate in  dichloromethane T=20°C; 1.5 h;   

Multi-step reaction with 2 steps 1: pTsOH / acetone2: PDC, pyridinium trifluoroacetate / 4 h / Ambient temperature