sodium hydroxide in ethanol 16 h;

1: With water; sodium hydroxide in ethanol T=55°C; 0.75 h; 2: With hydrogenchloride in ethanol; water T=20°C; 1.16667 h;

barium hydroxide octahydrate in methanol T=80°C; 1 h; Reflux;

ammonium acetate in butan-1-ol Rodionov reaction; Heating;

1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 - 35 °C / |Inert atmosphere 2.1: sodium hydroxide; water / ethanol / 0.75 h / 55 °C 2.2: 1.17 h / 20 °C View Scheme

pyridine

1: thionyl chloride; pyridine / N,N-dimethyl-formamide / chlorobenzene / 22 h / 120 °C / Inert atmosphere 2: triethylamine / 12 h / Reflux; Inert atmosphere View Scheme

1.1: triethylamine; chloroformic acid ethyl ester / 2-methyl tetrahydrofuran / 1 h / 10 - 20 °C / |Inert atmosphere 1.2: 2 h / 10 - 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 18 h / 20 - 40 °C / |Inert atmosphere 3.1: di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium; tri-cyclo-hexyl-phosphine; sodium tetraphenyl borate / dichloromethane; acetone / 14 h / 20 °C / |Inert atmosphere 4.1: 4-(dimethylamino)-N-((1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)picolinamide; tris(acetonitrile)(η5-2,4-cyclopentadien-1-yl)ruthenium(1+) hexafluorophosphate(1-); triphenoxyborane / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 5.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran; methanol / 20 h / 25 °C / 10343.2 Torr View Scheme

pyridine; thionyl chloride; N,N-dimethyl-formamide in chlorobenzene T=120°C; 22 h; Inert atmosphere;

1: thionyl chloride; pyridine / N,N-dimethyl-formamide / chlorobenzene / 22 h / 120 °C / Inert atmosphere 2: triethylamine / 12 h / Reflux; Inert atmosphere 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 13.5 h / 20 - 70 °C / Inert atmosphere 4: boron tribromide / dichloromethane / 2.5 h / -20 - 0 °C / Inert atmosphere View Scheme