Multi-step reaction with 10 steps
1: SOCl2, DMF / toluene / 0.5 h / Heating
2: NaN3 / acetone; H2O / 1 h
3: 1.5 h / Heating
4: 85 percent / K2CO3 / acetonitrile / 4 h / Heating
5: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature
6: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h
7: 78 percent / ethanol / 1.5 h / Heating
8: 82 percent / ethanol / 8 h / Heating
9: 89 percent / trimethyltin azide / toluene / 29 h / Heating
10: 40 percent / 1 N aq. NaOH / ethanol / 2 h / Ambient temperature
With
hydrogenchloride; sodium hydroxide; thionyl chloride; sodium azide; trimethyltin azide; potassium carbonate; pyrographite; hydrazine hydrate; N,N-dimethyl-formamide;
In
ethanol; water; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1021/jm00067a016