Multi-step reaction with 13 steps
1: sodium hydroxide / methanol; water / 0.17 h / Reflux
2: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 60 °C
3: potassium carbonate / dimethyl sulfoxide / 1 h / 20 °C
4: triethylamine / dichloromethane / 1 h / 0 °C
5: potassium iodide / N,N-dimethyl-formamide / 20 °C
6: hydrazine hydrate / ethanol / 1 h / Reflux
7: ethyl acetate / 2 h / 50 °C
8: potassium phosphate / dichloromethane; water / 1 h / 22 °C
9: potassium phosphate; dipotassium peroxodisulfate / acetonitrile; water / 1.5 h / 75 °C
10: trifluoroacetic acid / 3 h / 0 °C
11: triethylamine / acetonitrile / 40 h / 20 °C
12: sulfur trioxide pyridine complex / N,N-dimethyl-formamide / 20 °C
13: boron trichloride / dichloromethane; para-xylene
With
potassium phosphate; dipotassium peroxodisulfate; hydroxylamine hydrochloride; sodium acetate; sulfur trioxide pyridine complex; boron trichloride; potassium carbonate; hydrazine hydrate; triethylamine; trifluoroacetic acid; potassium iodide; sodium hydroxide;
In
methanol; ethanol; dichloromethane; para-xylene; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm400560z