hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium hydrogencarbonate; potassium hydrogencarbonate in (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; pyridine hydrochloride; ethyl acetate; butan-1-ol

potassium hydroxide; sodium hydroxide in butan-1-ol 24 h; Heating; Yield given;

aluminium trichloride in water

dicyclohexyl-carbodiimide in chloroform T=20°C; Cyclization; 5 h;

pyridine hydrochloride T=180°C; 3 h;

1: benzene / 2 h / Ambient temperature 2: AlCl3 / various solvent(s) / 20 h / Ambient temperature 3: 1 N NaOH / ethanol; H2O / 0.17 h / Heating 4: hydrazine hydrate, NaOCH3 / 2-methoxy-ethanol / 1.) from 60 deg C to 150 deg C, 2.) 150 deg C, 1 h 5: pyridine hydrochloride / 3 h / 180 °C View Scheme

1: 1 N NaOH / ethanol; H2O / 0.17 h / Heating 2: hydrazine hydrate, NaOCH3 / 2-methoxy-ethanol / 1.) from 60 deg C to 150 deg C, 2.) 150 deg C, 1 h 3: pyridine hydrochloride / 3 h / 180 °C View Scheme