1.1: 74 percent / dimethylformamide; H2O / 8 h / 70 °C 2.1: H2; NaHCO3 / Pd/C / methanol; H2O / 19 h / 50 °C / 760.05 Torr 2.2: 90 percent / aq. NaOH / methanol / 2 h / 60 °C 3.1: 95 percent / thionyl chloride / 40 - 45 °C 4.1: 78 percent / sodium borohydride / propan-2-ol; H2O / 2.5 h / 40 °C View Scheme

1.1: 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 2.1: hydrogen; K2CO3 / Pd-C / H2O; methanol; 1-methyl-pyrrolidin-2-one / 21.5 h / 45 °C / 760 Torr 2.2: 2.58 g / NaOH / H2O / 2 h / 50 °C / pH 13.0 3.1: 91 percent / 4-(dimethylamino)pyridine / dimethylformamide / 1.5 h / 45 °C 4.1: 70 percent / tetraethylammonium chloride; N,N-dimethylaniline; phosphorus oxychloride / acetonitrile / 1 h / 70 °C View Scheme

in N,N-dimethyl-formamide

1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 2: HCOONH4 / Pd/C / methanol / 4 h / Heating 3: aq. NaOH / 0.5 h / Heating 4: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 5: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 6: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 7: 99 percent / aq. MeNH2 / 0.25 h / 20 °C View Scheme

1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 2: HCOONH4 / Pd/C / methanol / 4 h / Heating 3: aq. NaOH / 0.5 h / Heating 4: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 5: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 6: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 7: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 8: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

1.1: 74 percent / dimethylformamide; H2O / 8 h / 70 °C 2.1: H2; NaHCO3 / Pd/C / methanol; H2O / 19 h / 50 °C / 760.05 Torr 2.2: 90 percent / aq. NaOH / methanol / 2 h / 60 °C 3.1: 95 percent / thionyl chloride / 40 - 45 °C 4.1: 70 percent / tetraethylammonium chloride; phosphorus oxychloride / acetonitrile / 1 h / 80 °C View Scheme

in N,N-dimethyl-formamide