Multi-step reaction with 9 steps
1: concd. H2SO4 / methanol
2: SOCl2, DMF / toluene / 0.5 h / Heating
3: NaN3 / acetone; H2O / 1 h
4: 1.5 h / Heating
5: 85 percent / K2CO3 / acetonitrile / 4 h / Heating
6: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature
7: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h
8: 96 percent / ethanol / 17 h / 50 °C
9: 1.) methyl iodide, 2.) HCl / 1.) EtOH, reflux, 24 h, 2.) EtOH, H2O
With
hydrogenchloride; thionyl chloride; sodium azide; sulfuric acid; potassium carbonate; pyrographite; hydrazine hydrate; N,N-dimethyl-formamide; methyl iodide;
In
methanol; ethanol; water; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1021/jm00067a016