Multi-step reaction with 8 steps
1: 1.) NaH / 1.) DMF, 60 deg C, 10 min, 2.) DMF, 60 deg C, 30 min
2: 92 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature
3: 0.5 h / 50 °C
4: 1.) HNO3, 2.) 2percent ethanol. HCl / 1.) from -20 deg C to -15 deg C, 30 min, 2.) reflux, 1 h
5: 100 percent / H2 / 10percent Pd/C / ethanol / 1.25 h / Ambient temperature
6: 1.) NaNO2, aq. HCl, 2.) Na2CO3 / 1.) from -5 deg C to 0 deg C, 2.) H2O, toluene, 50 deg C, 5 min
7: pyridine / 0.5 h
8: 1.) NaH / 1.) DMF, 5 min, 2.) DMF, 60 deg C, 30 min
With
pyridine; hydrogenchloride; lithium aluminium tetrahydride; hydrogen; nitric acid; sodium hydride; sodium carbonate; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol;
DOI:10.1021/jm00365a005