Multi-step reaction with 9 steps
1: 93 percent / K2CO3, NaI / acetone / 43 h / Heating
2: 2. NH4Cl / 1.) ether, reflux, 5 h, 2.) water
3: 94 percent / hydroquinone / 0.5 h / 200 °C
4: 2.) NH4OAc / 1.) 1,2-dichloroethane, reflux, 3 h, 2.) HAc, H2O, 100 deg C, 1 h
5: 84 percent / pyridine, piperidine / 3 h / 100 °C
6: 91 percent / H2 / Pd/C / ethanol / 10 h / 760 Torr
7: 95 percent / H2, 1.02 M HCl / Pd/C / ethanol / 31 h
8: 100 percent / dimethylformamide / 1 h / 25 °C
9: 98 percent / K2CO3 / dimethylformamide / 1 h / 25 °C
With
piperidine; pyridine; hydrogenchloride; ammonium acetate; hydrogen; potassium carbonate; ammonium chloride; hydroquinone; sodium iodide;
palladium on activated charcoal;
In
ethanol; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00172a032