ammonium chloride; zinc in methanol T=0 - 20°C; 1.16667 h;

1: With carbamic acid 1,1-dimethylethyl ester; caesium carbonate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; tris(dibenzylideneacetone)dipalladium(0) chloroform complex in toluene T=90°C; Inert atmosphere; 2: With trifluoroacetic acid in dichloromethane T=20°C; 1 h; Inert atmosphere;

thionyl chloride T=0°C; 12 h; Reflux;

1: With trifluoroacetic acid in dichloromethane T=20°C; 1 h; 2: With sodium hydrogencarbonate in water; ethyl acetate

1: sulfuric acid / 2 h / 60 °C 2: iron; acetic acid / ethanol / 2 h / Reflux View Scheme

1.1: sulfuric acid / 1 h / Inert atmosphere; Reflux 2.1: caesium carbonate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; carbamic acid 1,1-dimethylethyl ester / tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 90 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere View Scheme

1: chromium(VI) oxide; sulfuric acid; acetic acid / water / 2 h / 95 °C / Inert atmosphere 2: sulfuric acid / 1 h / 70 °C / Inert atmosphere 3: hydrazine hydrate / tetrahydrofuran; methanol / 70 °C / Inert atmosphere View Scheme

1.1: pyridine / dichloromethane / 15 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C 3.1: N-bromosuccinmide / dichloromethane / 10 - 20 °C 3.2: 2.5 h / 10 - 75 °C 4.1: ammonium hydroxide / water / 20 - 103 °C / sealed tube View Scheme

1.1: pyridine / dichloromethane / 15 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C 3.1: N-bromosuccinmide / dichloromethane / 10 - 20 °C 3.2: 2.5 h / 10 - 75 °C 4.1: ammonium hydroxide / water / 20 - 103 °C / sealed tube 5.1: acetonitrile; water / 20 - 60 °C View Scheme