1: durch Austausch von NH2 gegen Chlor 2: KOH-solution View Scheme

diethylaluminium chloride; boron trichloride in n-heptane; 1,2-dichloro-ethane 3 h; Heating / reflux;

1: Reaktion ueber mehrere Stufen 2: NaOH-solution 3: potassium permanganate; water 4: amyl alcohol; potash; copper powder View Scheme

1: durch Austausch von NH2 gegen Chlor 2: KOH-solution View Scheme

1: 86 percent / pyridine / ethyl acetate / 18 h / 20 °C 2: 48 percent / glacial AcOH; Br2 / 1.5 h / 15 °C 3: 94 percent / AcOH; conc. HCl / 24 h / 118 °C 4: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C 5: 93 percent / aq. KOH; H2O2 / 2 h / 130 °C 6: 97 percent / tetrahydrofuran / 6 h / 20 °C 7: 90 percent / DMAP / 3 h / 80 °C 8: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 9: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 10: 76 percent / 48percent aq. HBr / 7 h / 120 °C 11: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 12: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 13: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C 14: 80 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 15: 94 percent / Et3N / CH2Cl2 / 0.92 h 16: 77 percent / CH2Cl2 / 2.5 h / 20 °C 17: 0.142 g / TFA / CH2Cl2 / 0.92 h / 20 °C 18: PyBOP; diisopropylethylamine / dimethylformamide / 3 h View Scheme

in xylene 20 h; Heating;

1: methanol / 2 h / Heating 2: K2CO3 / toluene / 3 h / 40 °C View Scheme

1: 86 percent / pyridine / ethyl acetate / 18 h / 20 °C 2: 48 percent / glacial AcOH; Br2 / 1.5 h / 15 °C 3: 94 percent / AcOH; conc. HCl / 24 h / 118 °C 4: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C 5: 93 percent / aq. KOH; H2O2 / 2 h / 130 °C 6: 97 percent / tetrahydrofuran / 6 h / 20 °C 7: 90 percent / DMAP / 3 h / 80 °C 8: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 9: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 10: 76 percent / 48percent aq. HBr / 7 h / 120 °C 11: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C 12: 51 percent / NBS; dibenzoyl peroxide / CCl4 / 3.83 h / 85 °C / Irradiation 13: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C View Scheme

1: 86 percent / pyridine / ethyl acetate / 18 h / 20 °C 2: 48 percent / glacial AcOH; Br2 / 1.5 h / 15 °C 3: 94 percent / AcOH; conc. HCl / 24 h / 118 °C 4: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C 5: 93 percent / aq. KOH; H2O2 / 2 h / 130 °C 6: 97 percent / tetrahydrofuran / 6 h / 20 °C 7: 90 percent / DMAP / 3 h / 80 °C 8: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C 9: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C 10: 76 percent / 48percent aq. HBr / 7 h / 120 °C 11: 98 percent / DMAP; Et3N / CH2Cl2 / 0.5 h / 20 °C View Scheme

1: 86 percent / pyridine / ethyl acetate / 18 h / 20 °C 2: 48 percent / glacial AcOH; Br2 / 1.5 h / 15 °C 3: 94 percent / AcOH; conc. HCl / 24 h / 118 °C 4: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C View Scheme