1: K2CO3 / dimethylformamide / 70 °C 2: Fe; conc. HCl / ethanol / 2 h / Heating View Scheme

1: 94 percent / Et3N / CH2Cl2 / 12 h / 20 °C 2: H2 / 20percent Pd(OH)2/C / methanol / 12 h / 20 °C / 2585.81 Torr 3: aq. NH3 / methanol / 4 h / Heating View Scheme

1: 87 percent / CH2Cl2 / 1 h / Ambient temperature 2: 1.) aq. NaOH / 1.) MeOH, RT, 48 h, 2.) H2O, reflux, 1 h View Scheme

1.1: triethylamine / tetrahydrofuran / Inert atmosphere 2.1: 10 palladium on activated charcoal; hydrogen / ethanol 3.1: sodium carbonate / pentan-1-ol / Inert atmosphere 4.1: hydrogenchloride / ethanol; water / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 5 - 10 °C / Inert atmosphere; Large scale reaction 6.1: acetonitrile / 2 h / Reflux; Inert atmosphere; Large scale reaction 7.1: ethanol; acetyl chloride / 2 h / 45 °C / Inert atmosphere; Large scale reaction 8.1: triethylamine / dichloromethane / -10 °C / Inert atmosphere; Large scale reaction 9.1: methanesulfonic acid; water / 10 h / 70 °C / Inert atmosphere; Large scale reaction 9.2: Inert atmosphere; Large scale reaction View Scheme