hydrogen; palladium hydroxide - carbon in acetic acid P=2280 Torr; 10 h; Ambient temperature;

1: ethanol; H2O / 48 h / 55 °C 2: 1.) aq. NaOH, 2.) SOCl2 / 1.) reflux, overnight, 2.) reflux, 3 d 3: 100 percent / CH2Cl2 / Ambient temperature 4: 85 percent / H2 / 5percent Pd/C / ethanol / 4 h / 3102.9 Torr / Ambient temperature 5: 1.) HCl (gas), 2.) 1 N aq. NaOH / 1.) Et2O, RT, 1 h, 2.) THF, RT, overnight View Scheme

1: 98 percent / oxalyl chloride, DMSO / CH2Cl2 / 2 h / -78 °C 2: ethanol; H2O / 48 h / 55 °C 3: 1.) aq. NaOH, 2.) SOCl2 / 1.) reflux, overnight, 2.) reflux, 3 d 4: 100 percent / CH2Cl2 / Ambient temperature 5: 85 percent / H2 / 5percent Pd/C / ethanol / 4 h / 3102.9 Torr / Ambient temperature 6: 1.) HCl (gas), 2.) 1 N aq. NaOH / 1.) Et2O, RT, 1 h, 2.) THF, RT, overnight View Scheme

1: i-Pr2NEt / CH2Cl2 / Ambient temperature 2: 98 percent / oxalyl chloride, DMSO / CH2Cl2 / 2 h / -78 °C 3: ethanol; H2O / 48 h / 55 °C 4: 1.) aq. NaOH, 2.) SOCl2 / 1.) reflux, overnight, 2.) reflux, 3 d 5: 100 percent / CH2Cl2 / Ambient temperature 6: 85 percent / H2 / 5percent Pd/C / ethanol / 4 h / 3102.9 Torr / Ambient temperature 7: 1.) HCl (gas), 2.) 1 N aq. NaOH / 1.) Et2O, RT, 1 h, 2.) THF, RT, overnight View Scheme

1: 100 percent / CH2Cl2 / Ambient temperature 2: 85 percent / H2 / 5percent Pd/C / ethanol / 4 h / 3102.9 Torr / Ambient temperature 3: 1.) HCl (gas), 2.) 1 N aq. NaOH / 1.) Et2O, RT, 1 h, 2.) THF, RT, overnight View Scheme

1: 1.) aq. NaOH, 2.) SOCl2 / 1.) reflux, overnight, 2.) reflux, 3 d 2: 100 percent / CH2Cl2 / Ambient temperature 3: 85 percent / H2 / 5percent Pd/C / ethanol / 4 h / 3102.9 Torr / Ambient temperature 4: 1.) HCl (gas), 2.) 1 N aq. NaOH / 1.) Et2O, RT, 1 h, 2.) THF, RT, overnight View Scheme

1: 85 percent / H2 / 5percent Pd/C / ethanol / 4 h / 3102.9 Torr / Ambient temperature 2: 1.) HCl (gas), 2.) 1 N aq. NaOH / 1.) Et2O, RT, 1 h, 2.) THF, RT, overnight View Scheme

1: H2SO4 / 240 h / Heating 2: i-Pr2NEt / CH2Cl2 / Ambient temperature 3: 98 percent / oxalyl chloride, DMSO / CH2Cl2 / 2 h / -78 °C 4: ethanol; H2O / 48 h / 55 °C 5: 1.) aq. NaOH, 2.) SOCl2 / 1.) reflux, overnight, 2.) reflux, 3 d 6: 100 percent / CH2Cl2 / Ambient temperature 7: 85 percent / H2 / 5percent Pd/C / ethanol / 4 h / 3102.9 Torr / Ambient temperature 8: 1.) HCl (gas), 2.) 1 N aq. NaOH / 1.) Et2O, RT, 1 h, 2.) THF, RT, overnight View Scheme

1: H2 / 20percent Pd(OH)2/C / methanol / 2 h / 750.06 Torr 2: 48 percent / 6 N HCl / 27.5 h / Heating View Scheme

1: triethylamine / CH2Cl2 / 6 h / Heating 2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, from -78 deg C to RT 3: ethanol; H2O / 24 h / 55 - 60 °C 4: 64 percent / 6 N aq. HCl / 24 h / 130 °C 5: 76 percent / H2 / 20percent Pd(OH)2-C / aq. acetic acid / 10 h / 2280 Torr / Ambient temperature View Scheme