1: 2) conc. HCl / 1) benzene, reflux, 35 h, 2) H2O, warming, 30 min 2: 94 percent / H2 / 10percent Pd-C / methanol / 24 h / 760 Torr / Ambient temperature View Scheme

hydrogen; palladium on activated charcoal Multistep reaction;

1: 2.) 12percent hydrochloric acid / 1.) heptane, 90-95 deg C, 9 h; 2.) 20-25 deg C, 5 h.; CHCl3 2: 96.5 percent / hydrogen, acetic acid / Pd/ BaSO4 / ethanol 3: 74 percent / KOH / aq. ethanol / 10 h / 95 - 100 °C View Scheme

in chloroform Ambient temperature;

(i) Et3N, CHCl3, (ii) NaOH, N(CH2CH2OH)3, (iii) N2H4*H2O; Multistep reaction;

1: (i) Et3N, CHCl3, (ii) NaOH, N(CH2CH2OH)3, (iii) N2H4*H2O 2: HBr / acetic acid View Scheme