1: 80 percent / H2 / 5percent Pd on charcoal / ethanol / Ambient temperature 2: 1.) conc. HCl, NaNO2; 2.) Cu2Cl2, conc. HCl / 1.) -6 deg C - 7 deg C; 2.) room temp., 1 h. 3: 10percent aq HCl / ethanol / 3 h / 120 - 130 °C View Scheme

1: 31 percent / KF / dimethylsulfoxide / 1 h / 165 °C 2: 95 percent / 10percent aq. HCl / ethanol / 3 h / 120 °C 3: 78 percent / pyridine / 1 h / 105 - 113 °C View Scheme

1: 31 percent / KF / dimethylsulfoxide / 1 h / 165 °C 2: 95 percent / 10percent aq. HCl / ethanol / 3 h / 120 °C View Scheme

1: 80 percent / H2 / 5percent Pd on charcoal / ethanol / Ambient temperature 2: 1.) conc. HCl, NaNO2; 2.) Cu2Cl2, conc. HCl / 1.) -6 deg C - 7 deg C; 2.) room temp., 1 h. View Scheme

potassium fluoride in dimethyl sulfoxide T=165°C; 1 h;

With  hydrogen; palladium on activated charcoal in  ethanol  Ambient temperature;