1: Schotten-Baumann reaction 2: 97 percent / PPh3, CBr4 / Heating 3: 21 percent / hexane / 0.3 h / 0 °C / Irradiation View Scheme

tributyl-amine; palladium diacetate in xylene T=120°C; 2 h;

1: in pyridine T=70 - 75°C; Baker-Venkataraman synthesis; 12 h; Heating; 2: With potassium hydroxide in pyridine T=60 - 70°C; 5 h; 3: With sulfuric acid in acetic acid T=60 - 70°C; 5 h; Heating;

1: 1.27 g / pyridine 2: KOH / pyridine / 48 h / Ambient temperature View Scheme

1.1: ammonia / acetone / 1 h / 0 - 20 °C 2.1: NaClO; sodium hydroxide / water / 20 - 100 °C 3.1: sulfuric acid; sodium nitrite / water / 10 - 15 °C 3.2: 2 h / 100 °C View Scheme

1: morpholine With potassium carbonate in tetrahydrofuran T=20°C; 0.25 h; 2: 3,4,5-trimethoxy-benzoic acid chloride in tetrahydrofuran T=20°C; 48 h;

1.1: zinc-copper couple / benzene; N,N-dimethyl-acetamide / 3 h / 20 °C / sonication 1.2: 31 percent / bis(triphenylphosphine)palladium dichloride / benzene; N,N-dimethyl-acetamide / 2 h / sonication 2.1: 91 percent / H2 / Pd/C / ethanol; H2O / 22 h / 3102.89 Torr 3.1: 93 percent / NaHCO3; silver trifluoroacetate; I2 / CHCl3 / 2 h / 0 °C 4.1: trifluoroacetic acid / diethyl ether / 3 h / 20 °C 5.1: 454 mg / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h 6.1: 60 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 15 h / 90 °C 7.1: 91 percent / potassium carbonate / methanol / 11 h / 20 °C 8.1: 100 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C 9.1: potassium carbonate / methanol / 1 h / Heating 9.2: 64 percent / KOH / methanol / 3 h / Heating 10.1: 70 percent / various solvent(s) / 40 h / Heating 11.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 12.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 13.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 14.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 15.1: HCl / diethyl ether / 1 h / 20 °C 15.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme

Hydrogenation;

benzyl-N,N-dimethylamine; palladium diacetate in xylene T=120°C; 4.5 h;

in cyclohexane; acetone; toluene