1: ueber 6,7-Dimethoxy-1,2,3,4-tetrahydro-<1>naphthylamin 2: palladium/charcoal; 1-isopropyl-4-methyl-benzene View Scheme

pyridine; hydroxylamine hydrochloride T=25°C; 3 h; Inert atmosphere;

1: concentrated sulfuric acid View Scheme

1.1: sodium hydride / tetrahydrofuran; dimethyl sulfoxide; mineral oil / 0.17 h / 0 °C / |Inert atmosphere 1.2: 20 h / 0 - 20 °C / |Inert atmosphere 2.1: palladium on activated charcoal / methanol / 0.17 h / 20 °C / |Inert atmosphere 2.2: 4 h / |Inert atmosphere 3.1: polyphosphoric acid / dichloromethane / 4 h / |Inert atmosphere; |Reflux 4.1: pyridine; hydroxylamine hydrochloride / 4 h / 20 °C / |Inert atmosphere View Scheme

1.1: palladium on activated charcoal / methanol / 0.17 h / 20 °C / |Inert atmosphere 1.2: 4 h / |Inert atmosphere 2.1: polyphosphoric acid / dichloromethane / 4 h / |Inert atmosphere; |Reflux 3.1: pyridine; hydroxylamine hydrochloride / 4 h / 20 °C / |Inert atmosphere View Scheme

1: aluminium chloride; nitrobenzene 2: amalgamated zinc; aqueous hydrochloric acid; toluene / weiteres Reagens: Essigsaeure 3: concentrated sulfuric acid View Scheme

1: amalgamated zinc; aqueous hydrochloric acid; toluene / weiteres Reagens: Essigsaeure 2: concentrated sulfuric acid View Scheme

1: ueber 6,7-Dimethoxy-1,2,3,4-tetrahydro-<1>naphthylamin 2: palladium/charcoal; 1-isopropyl-4-methyl-benzene 3: aqueous H2SO4 View Scheme