1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 2: 82 percent / pyridine / 1 h / 20 °C 3: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 4: 91 percent / acetone / 3 h 5: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C View Scheme

1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 2: 82 percent / pyridine / 1 h / 20 °C 3: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 4: 91 percent / acetone / 3 h View Scheme

1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 2: 82 percent / pyridine / 1 h / 20 °C 3: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 4: 91 percent / acetone / 3 h 5: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 6: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme

1: Fe, AcOH / H2O; methanol 2: (i) aq. HBr, NaNO2, (ii) CuBr, aq. HBr 3: Cu, 4-methoxy-phenol <K salt> / 220 - 230 °C View Scheme

1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 2: 82 percent / pyridine / 1 h / 20 °C 3: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 4: 70 percent aq. HClO4 / 1 h / 20 °C 5: H2O / 0.08 h / Heating View Scheme

hydrogenchloride; iron in ethanol T=65 - 70°C; Reduction; 0.333333 h;