potassium carbonate in N,N-dimethyl acetamide; water

1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 125 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere View Scheme

1: ethanol / 24 h / Ambient temperature 2: methanol / 12 h / Ambient temperature View Scheme

1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 125 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere 3: palladium 10 on activated carbon; hydrazine hydrate / ethanol / 3.5 h / Reflux; Inert atmosphere 4: pyridine / acetonitrile / 0 - 20 °C / Inert atmosphere View Scheme

1.1: pyridine / 4 h / 0 - 20 °C 2.1: sodium hydroxide / water / 48 h / Reflux 2.2: 20 °C / pH 4 View Scheme

potassium hydroxide in N-methyl-acetamide; anhydrous xylene; ethyl acetate