methanol; sodium methylate T=0°C; 2 h;

hydrogen; palladium on activated charcoal in methanol P=760 Torr; 2 h; Ambient temperature;

sodium methylate in methanol T=0°C;

1: H2 / Pd/C / ethyl acetate / 0.25 h / 25 °C / 2068.6 Torr 2: 96 percent / MeOH, MeONa / 2 h / 0 °C View Scheme

1: 45 percent / KOH / dimethylsulfoxide / 5 h / Ambient temperature 2: 70 percent / NaH / dimethylformamide; CH2Cl2 / 5 h / Ambient temperature 3: 72 percent / H2 / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: 64 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiiimide / tetrahydrofuran; H2O / 1 h / Ambient temperature 2: Ph3P, diethylazodicarboxylate / tetrahydrofuran / 16 h / Ambient temperature 3: 93 percent / quinoline, H2 / 5percent Pd/C / ethanol / 1 h / 760 Torr / Ambient temperature 4: 45 percent / KOH / dimethylsulfoxide / 5 h / Ambient temperature 5: 70 percent / NaH / dimethylformamide; CH2Cl2 / 5 h / Ambient temperature 6: 72 percent / H2 / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: 93 percent / quinoline, H2 / 5percent Pd/C / ethanol / 1 h / 760 Torr / Ambient temperature 2: 45 percent / KOH / dimethylsulfoxide / 5 h / Ambient temperature 3: 70 percent / NaH / dimethylformamide; CH2Cl2 / 5 h / Ambient temperature 4: 72 percent / H2 / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: Ph3P, diethylazodicarboxylate / tetrahydrofuran / 16 h / Ambient temperature 2: 93 percent / quinoline, H2 / 5percent Pd/C / ethanol / 1 h / 760 Torr / Ambient temperature 3: 45 percent / KOH / dimethylsulfoxide / 5 h / Ambient temperature 4: 70 percent / NaH / dimethylformamide; CH2Cl2 / 5 h / Ambient temperature 5: 72 percent / H2 / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: 70 percent / NaH / dimethylformamide; CH2Cl2 / 5 h / Ambient temperature 2: 72 percent / H2 / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: 1 N NaOH / tetrahydrofuran / 1 h / Ambient temperature 2: 64 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiiimide / tetrahydrofuran; H2O / 1 h / Ambient temperature 3: Ph3P, diethylazodicarboxylate / tetrahydrofuran / 16 h / Ambient temperature 4: 93 percent / quinoline, H2 / 5percent Pd/C / ethanol / 1 h / 760 Torr / Ambient temperature 5: 45 percent / KOH / dimethylsulfoxide / 5 h / Ambient temperature 6: 70 percent / NaH / dimethylformamide; CH2Cl2 / 5 h / Ambient temperature 7: 72 percent / H2 / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature View Scheme