Multi-step reaction with 11 steps
1: 71 percent / K2CO3 / dimethylformamide / Ambient temperature; overnight
2: 95 percent / AlCl3 / CH2Cl2 / Ambient temperature
3: 88 percent / K2CO3 / butan-2-one / 2 h / Heating
4: H2 / 5percent sulfided Pt/C / ethanol
5: 1.) NaNO2, H2SO4, 2.) Na2SO4, H2SO4 / 1.) H2O, RT, overnight, 2.) H2O, reflux, 2 h
6: H2SO4 / 2.5 h / Heating
7: H2SO4 / acetic acid / Ambient temperature
8: H2SO4 / Ambient temperature
9: HCl / ethanol / 4 h / Heating
10: 1.36 g / Et3N / dimethylformamide / 2.5 h / Ambient temperature
11: 97 percent / diisopropylethylamine / CH2Cl2 / 1 h
With
hydrogenchloride; aluminium trichloride; sulfuric acid; hydrogen; potassium carbonate; sodium sulfate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium nitrite;
sulfided Pt/C;
In
ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; butanone;
DOI:10.1021/jm00379a016