Multi-step reaction with 9 steps
1: 100 percent / triethylamine / CHCl3 / 4 h / 0 °C
2: 28 percent / fuming nitric acid, acetic anhydride, conc. sulfuric acid / 4 h / Ambient temperature
3: 78 percent / K2CO3 / dimethylformamide / 15 h / Ambient temperature
4: 90 percent / iron, conc. hydrochloric acid / methanol / 8 h / Heating
5: 93 percent / NaBH4, / methanol; tetrahydrofuran / 27 h / Heating
6: 92 percent / SO2Cl, DMF / CHCl3 / 1 h / Heating
7: 94 percent / dimethylformamide / 22 h / Ambient temperature
8: 100 percent / HCl / 2.5 h / Heating
9: 56 percent / NaN3, NH4Cl / dimethylformamide / 84 h / 110 - 120 °C
With
hydrogenchloride; sodium tetrahydroborate; sodium azide; sulfuryl dichloride; sulfuric acid; nitric acid; acetic anhydride; iron; potassium carbonate; ammonium chloride; triethylamine; N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jm00064a011