Multi-step reaction with 9 steps
1: 1.) NaNO2, HCl, 2.) CuCl2*2H2O, HOAc, SO2 / 1.) H2O, 2.) H2O, RT
2: 90 percent / NH3 / Ambient temperature
3: 87 percent / dimethylformamide / 30 h / 60 °C
4: 94 percent / fuming sulfuric acid (20percent SO2), fuming HNO3 / 2 h / 55 °C
5: 90 percent / H2 / 5percent Pd/C / tetrahydrofuran / 20 °C / 75.01 Torr
6: 91 percent / 2N aq. NaOH / methanol / 1 h / Ambient temperature
7: 1.) NaNO2, HCl, HOAc, 2.) CuCl2*2H2O, HOAc, SO2 / 1.) H2O, 2.) H2O
8: 92 percent / H2O / 0.5 h / 100 °C
9: dioxane / 1 h / 85 °C
With
hydrogenchloride; sodium hydroxide; sulfuric acid; sulfur dioxide; sulfur trioxide; ammonia; water; hydrogen; nitric acid; acetic acid; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jm00362a017