Multi-step reaction with 8 steps
1: 84 percent / pyridine, KOH / 24 h / 25 °C
2: 1) conc. H2SO4, 2) aq. HBr / 1) 80 deg C, 2 h, 2) reflux, 8 h
3: 87 percent / HCl / 16 h
4: 90 percent / H2 / 5percent Pd/C / aq. ethanol / 24 h / 1810.02 Torr
5: 1) aq. NaNO2, aq. H2SO4 / 1) 0 deg C, 30 min, 2) rt, 72 h
6: 94 percent / aq. KOH / 2 h / 80 °C
7: 1) H2O, 2) aq. NaHCO3 / 1) 4 h, 2) ethyl acetate, rt, 36 h, pH 7.8
8: 87 percent / 10 h / 120 °C
With
pyridine; hydrogenchloride; potassium hydroxide; sulfuric acid; water; hydrogen bromide; hydrogen; sodium hydrogencarbonate; sodium nitrite;
palladium on activated charcoal;
In
ethanol;
DOI:10.1021/jm00127a020