sodium hydroxide in methanol 27 h; Heating;

quinoline; hydrogen; Lindlar's catalyst in ethyl acetate T=37°C; Yield given;

1: 100 percent / 15 h / 140 °C 2: 1.) 1M NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, r.t., 15 h 3: diethyl ether 4: 97 percent / H2 / 10percent Pd/C / ethyl acetate 5: 90 percent / NaOMe / methanol / Ambient temperature 6: 80 percent / pyridinium chlorochromate / CH2Cl2 / warming with a H2O bath 7: 1.) NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) -20 deg C , 1 h, b) r.t., 15 h 8: TsOH / methanol 9: 93 percent / NaOH / methanol / 27 h / Heating View Scheme

1: 87 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 1.) 1M NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, r.t., 15 h 3: diethyl ether 4: 97 percent / H2 / 10percent Pd/C / ethyl acetate 5: 90 percent / NaOMe / methanol / Ambient temperature 6: 80 percent / pyridinium chlorochromate / CH2Cl2 / warming with a H2O bath 7: 1.) NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) -20 deg C , 1 h, b) r.t., 15 h 8: TsOH / methanol 9: 93 percent / NaOH / methanol / 27 h / Heating View Scheme

1: 1.) 1M NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, r.t., 15 h 2: diethyl ether 3: 97 percent / H2 / 10percent Pd/C / ethyl acetate 4: 90 percent / NaOMe / methanol / Ambient temperature 5: 80 percent / pyridinium chlorochromate / CH2Cl2 / warming with a H2O bath 6: 1.) NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) -20 deg C , 1 h, b) r.t., 15 h 7: TsOH / methanol 8: 93 percent / NaOH / methanol / 27 h / Heating View Scheme

1: 1.) 1M NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, r.t., 15 h 2: diethyl ether 3: 97 percent / H2 / 10percent Pd/C / ethyl acetate 4: 90 percent / NaOMe / methanol / Ambient temperature 5: 80 percent / pyridinium chlorochromate / CH2Cl2 / warming with a H2O bath 6: 1.) NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) -20 deg C , 1 h, b) r.t., 15 h 7: TsOH / methanol 8: 93 percent / NaOH / methanol / 27 h / Heating View Scheme

1: 97 percent / H2 / 10percent Pd/C / ethyl acetate 2: 90 percent / NaOMe / methanol / Ambient temperature 3: 80 percent / pyridinium chlorochromate / CH2Cl2 / warming with a H2O bath 4: 1.) NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) -20 deg C , 1 h, b) r.t., 15 h 5: TsOH / methanol 6: 93 percent / NaOH / methanol / 27 h / Heating View Scheme

1: 51.2 percent / BuLi / hexamethylphosphoric acid triamide / 20 h / 0 °C 2: 95 percent / p-toluenesulphonic acid monohydrate / tetrahydrofuran; acetic acid; H2O / 6 h / Heating 3: H2, quinoline / Lindlar's catalyst / ethyl acetate / 37 °C View Scheme

1: 91.7 percent / KOH, potassium hypobromite / H2O / 2.5 h / -5 °C 2: 41.9 percent / ethylamine/CuCl, NH2OH*HCl / methanol / 3 h / 10 °C 3: 93.6 percent / H2 / Pt / methanol / 0 °C / 750.06 Torr 4: 100 percent / p-toluenesulphonic acid monohydrate / tetrahydrofuran; acetic acid; H2O / 7 h / Heating 5: 82.1 percent / 48percent HBr / acetic acid / 28 h / 122 - 123 °C 6: 51.2 percent / BuLi / hexamethylphosphoric acid triamide / 20 h / 0 °C 7: 95 percent / p-toluenesulphonic acid monohydrate / tetrahydrofuran; acetic acid; H2O / 6 h / Heating 8: H2, quinoline / Lindlar's catalyst / ethyl acetate / 37 °C View Scheme

1: 82.1 percent / 48percent HBr / acetic acid / 28 h / 122 - 123 °C 2: 51.2 percent / BuLi / hexamethylphosphoric acid triamide / 20 h / 0 °C 3: 95 percent / p-toluenesulphonic acid monohydrate / tetrahydrofuran; acetic acid; H2O / 6 h / Heating 4: H2, quinoline / Lindlar's catalyst / ethyl acetate / 37 °C View Scheme