Multi-step reaction with 9 steps
1.1: sulfuric acid; potassium nitrate / 24 h / 0 - 20 °C
2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 18 h / 20 °C
3.1: sodium azide / dichloromethane / 0.5 h / 20 °C
3.2: 3 h / Reflux
4.1: palladium on activated charcoal; hydrogen / methanol / 15 h
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 20 °C
6.1: hydrogenchloride / ethyl acetate; 1,4-dioxane / 5 h / 20 °C
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C
8.1: palladium on activated charcoal; hydrogen / methanol / 1 h
9.1: pyridine / dichloromethane / 2 h / 50 °C
With
pyridine; hydrogenchloride; sodium azide; oxalyl dichloride; sulfuric acid; palladium on activated charcoal; hydrogen; potassium nitrate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; lithium hexamethyldisilazane;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate;