1: 92 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature 2: 60 percent / hydrazine hydrate, glacial acetic acid / ethanol / 1.5 h / Ambient temperature 3: 85 percent / Hg(II)-acetate / 1) 75 deg , 2 h; 2) 1 h, reflux 4: 58 percent / 1 h / 200 °C 5: 94 percent / H2 / Pt-oxide / acetic acid / 1 h 6: 62 percent / K2CO3 / 16 h / Ambient temperature 7: 6 h / 60 °C 8: 15 percent HCl / 1) 16 h, r.t.; 2) 30 min, 60 deg C 9: 98 percent / H2 / Pd/C / acetic acid / 1 h / Ambient temperature View Scheme

With  pyridine; chromium(VI) oxide in  dichloromethane 0.25 h;  Ambient temperature;   

Multi-step reaction with 3 steps 1: 92 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature2: 60 percent / hydrazine hydrate, glacial acetic acid / ethanol / 1.5 h / Ambient temperature3: 99 percent / 4-methylmorpholine / diethyl ether / 20 h / Ambient temperature  

Multi-step reaction with 4 steps 1: 92 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature2: 60 percent / hydrazine hydrate, glacial acetic acid / ethanol / 1.5 h / Ambient temperature3: 99 percent / 4-methylmorpholine / diethyl ether / 20 h / Ambient temperature4: 85 percent / 1 h / 200 °C  

Multi-step reaction with 3 steps 1: 92 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature2: 60 percent / hydrazine hydrate, glacial acetic acid / ethanol / 1.5 h / Ambient temperature3: 85 percent / Hg(II)-acetate / 1) 75 deg , 2 h; 2) 1 h, reflux  

Multi-step reaction with 4 steps 1: 92 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature2: 60 percent / hydrazine hydrate, glacial acetic acid / ethanol / 1.5 h / Ambient temperature3: 85 percent / Hg(II)-acetate / 1) 75 deg , 2 h; 2) 1 h, reflux4: 58 percent / 1 h / 200 °C  

Multi-step reaction with 6 steps 1: 92 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature2: 60 percent / hydrazine hydrate, glacial acetic acid / ethanol / 1.5 h / Ambient temperature3: 85 percent / Hg(II)-acetate / 1) 75 deg , 2 h; 2) 1 h, reflux4: 58 percent / 1 h / 200 °C5: 94 percent / H2 / Pt-oxide / acetic acid / 1 h6: 62 percent / K2CO3 / 16 h / Ambient temperature  

Multi-step reaction with 7 steps 1: 92 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature2: 60 percent / hydrazine hydrate, glacial acetic acid / ethanol / 1.5 h / Ambient temperature3: 85 percent / Hg(II)-acetate / 1) 75 deg , 2 h; 2) 1 h, reflux4: 58 percent / 1 h / 200 °C5: 94 percent / H2 / Pt-oxide / acetic acid / 1 h6: 62 percent / K2CO3 / 16 h / Ambient temperature7: 6 h / 60 °C  

Multi-step reaction with 8 steps 1: 92 percent / CrO3, pyridine / CH2Cl2 / 0.25 h / Ambient temperature2: 60 percent / hydrazine hydrate, glacial acetic acid / ethanol / 1.5 h / Ambient temperature3: 85 percent / Hg(II)-acetate / 1) 75 deg , 2 h; 2) 1 h, reflux4: 58 percent / 1 h / 200 °C5: 94 percent / H2 / Pt-oxide / acetic acid / 1 h6: 62 percent / K2CO3 / 16 h / Ambient temperature7: 6 h / 60 °C8: 15 percent HCl / 1) 16 h, r.t.; 2) 30 min, 60 deg C