potassium hydroxide in diethyl ether T=120°C; 2 h;

sodium hydroxide in ethanol; water

sodium hydroxide in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=80°C; 5.5 h;

1: 1.) NaNO2, hydrochloric acid, 2.) hydrated CuSO4, anhyd. NaSO3, NaOAc. 3.) hydrochloric acid 2: 70 percent / NaOAc / acetic acid / 6 h 3: 85 percent / alkaline hydrolysis 4: 30 percent / NaOH / hexamethylphosphoric acid triamide / 5.5 h / 80 °C View Scheme

1: 70 percent / NaOAc / acetic acid / 6 h 2: 85 percent / alkaline hydrolysis 3: 30 percent / NaOH / hexamethylphosphoric acid triamide / 5.5 h / 80 °C View Scheme

1: 85 percent / alkaline hydrolysis 2: 30 percent / NaOH / hexamethylphosphoric acid triamide / 5.5 h / 80 °C View Scheme

quinoline; copper