methanol; sodium hydroxide; water

1: 4-hydroxyindazole With sodium hydride in N,N-dimethyl-formamide T=20°C; 0.166667 h; 2: benzyl bromide in N,N-dimethyl-formamide T=20°C; 2 h;

1: With potassium acetate; acetic anhydride in toluene 3.5 h; 2: With isopentyl nitrite in toluene T=80°C; 18 h; 3: With tetra(n-butyl)ammonium hydroxide; sodium hydroxide in methanol T=40°C; 4 h;

1.1: lithium tetramethylpiperidine / hexane; diethyl ether / 0.25 h / -78 °C 1.2: hexane; diethyl ether / 8.5 h / Heating 2.1: KOH / ethanol View Scheme

1.1: hydrogen; 3 platinum on carbon / ethanol / 21.5 h / 258.58 - 2585.81 Torr 2.1: potassium acetate; acetic anhydride / toluene / 3.5 h 2.2: 18 h / 80 °C 2.3: 4 h / 40 °C View Scheme

1.1: caesium carbonate / N,N-dimethyl-formamide / 5.25 h / 40 - 90 °C 2.1: hydrogen; palladium(II) oxide hydrate / tert-butyl methyl ether / 12 h / 2430.66 Torr / |Inert atmosphere 3.1: tert-butyl methyl ether / 760.05 Torr / |Heating; |Inert atmosphere 3.2: 36 h / 65 °C / |Heating; |Inert atmosphere 4.1: potassium hydroxide / tetrahydrofuran; water / 3 h View Scheme