Multi-step reaction with 11 steps
1: 81 percent / fuming HNO3 / -20 °C
2: 79 percent / 1.) FeSO4, aq. HCl, 2.) 15 N ammonium hydroxide; / 90 °C
3: 1.) aq. HCl, NaNO2, 2.) Cu2Cl2; / 1.) water, 0 deg C, 2.) temperature below 5 deg C, 3.) heating on steam bath, 1 h;
4: 89 percent / NaBH4 / propan-2-ol / 1 h / 70 °C
5: 60 percent / K2CO3 / dimethylformamide / 36 h / Ambient temperature
6: 100 percent / SOCl2 / CH2Cl2 / 1.5 h / Heating
7: 64 percent / dimethylsulfoxide / 3 h / Ambient temperature
8: 87 percent / aq. 25percent NaOH / ethanol / Heating; overnight
9: SOCl2 / CH2Cl2 / 2.5 h / Heating
10: K2CO3 / H2O; CH2Cl2; toluene / 1 h
11: 77 percent / 1.) borane-tetrahydrofuran, 2.) methanol; / Heating; 1.) THF, reflux, 1.5 h, 2.) reflux, 2 h;
With
copper(I) chloride; hydrogenchloride; methanol; ammonium hydroxide; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; borane-THF; nitric acid; potassium carbonate; iron(II) sulfate; sodium nitrite;
In
ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1002/jhet.5570230641