Multi-step reaction with 11 steps
1: potassium carbonate / dichloromethane / 18 h / 0 - 20 °C
2: potassium carbonate / acetonitrile / 18 h / Heating / reflux
3: sulfuric acid; nitric acid / water / 0.5 h / -5 °C
4: methanol; potassium carbonate / 1 h / 20 °C
5: potassium carbonate / acetonitrile / 18 h / Heating / reflux
6: hydrogen / palladium 10% on activated carbon / methanol / 3 h / 1551.49 Torr
7: tert.-butylnitrite; boron trifluoride diethyl etherate / 1,2-dimethoxyethane / 2 h / -4 °C
8: 1,2,4-Trichlorobenzene / 18 h / 110 °C
9: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C
10: pyridine; thionyl chloride / tetrahydrofuran / 1 h / 0 - 20 °C
11: N,N-dimethyl-formamide / 18 h / 60 °C
With
pyridine; methanol; lithium aluminium tetrahydride; thionyl chloride; tert.-butylnitrite; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; nitric acid; potassium carbonate;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1,2,4-Trichlorobenzene;