1: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 2: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

With  toluene-4-sulfonic acid in  ethanol T=45°C;   

Multi-step reaction with 2 steps 1: 81 percent / potassium fluoride dihydrate / dimethylformamide / 5 h2: 78 percent / n-butylamine, cuprous iodide / tetrakis (triphenylphosphine) palladium / benzene / 6 h / Ambient temperature  

Multi-step reaction with 3 steps 1: 69 percent / NaBH4, H2, Ni(OAc)2 * 4 H2O / ethanol2: 81 percent / potassium fluoride dihydrate / dimethylformamide / 5 h3: 78 percent / n-butylamine, cuprous iodide / tetrakis (triphenylphosphine) palladium / benzene / 6 h / Ambient temperature