1: N,N-Diisopropyl-3-pyridinecarboxamide With lithium diisopropyl amide in tetrahydrofuran; n-heptane; ethylbenzene T=-80°C; 0.25 h; 2: N,N-dimethyl benzamide in tetrahydrofuran; n-heptane; ethylbenzene T=-80 - 20°C; 3 h;

lithium diisopropyl amide 1.) Et2O, C6H6, -78 deg C, 1 h, 2.) -78 deg C, 2 h; 25 deg C, 1.5 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 81 percent / NaBH4 / ethanol / 1.5 h / 20 °C 2: 98 percent / HCOOH / 23 h / Heating 3: aq. Na2CO3 / methanol / 2 h / 20 °C 4: 0.120 g / MnO2 / acetone / 24 h / 20 °C View Scheme

1: 81 percent / NaBH4 / ethanol / 1.5 h / 20 °C 2: 98 percent / HCOOH / 23 h / Heating 3: aq. Na2CO3 / methanol / 2 h / 20 °C 4: 0.120 g / MnO2 / acetone / 24 h / 20 °C 5: SOCl2 / 2.5 h / 60 °C 6: 120 mg / aq. NH4OH / acetone / 1.5 h / 20 °C View Scheme