in methanol; water

disodium hydrogenphosphate in acetonitrile T=20°C; 18 h; Inert atmosphere;

1: 2-amino-3-methoxy-benzoic acid With hydrogenchloride; sodium nitrite in water T=0°C; 2: With potassium iodide in dichloromethane; water T=0 - 20°C; Sandmeyer reaction; 3: methyl iodide With potassium carbonate in N,N-dimethyl-formamide 16 h;

1.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1.1 h / -78 °C / Inert atmosphere 1.2: 8 h / -78 - 20 °C / Inert atmosphere 2.1: disodium hydrogenphosphate / acetonitrile / 18 h / 20 °C / Inert atmosphere View Scheme

1.1: tetrahydrofuran / Inert atmosphere 2.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1.1 h / -78 °C / Inert atmosphere 2.2: 8 h / -78 - 20 °C / Inert atmosphere 3.1: disodium hydrogenphosphate / acetonitrile / 18 h / 20 °C / Inert atmosphere View Scheme

1.1: thionyl chloride; N,N-dimethyl-formamide / Inert atmosphere 2.1: tetrahydrofuran / Inert atmosphere 3.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1.1 h / -78 °C / Inert atmosphere 3.2: 8 h / -78 - 20 °C / Inert atmosphere 4.1: disodium hydrogenphosphate / acetonitrile / 18 h / 20 °C / Inert atmosphere View Scheme

1: aqueous sulfuric acid; sodium nitrite / Eintragen der erhaltenen Diazoniumsalz-Loesung in eine heisse wss. Loesung von Kaliumjodid 2: sulfuric acid View Scheme

1: platinum; ethanol / Hydrogenation 2: aqueous sulfuric acid; sodium nitrite / Eintragen der erhaltenen Diazoniumsalz-Loesung in eine heisse wss. Loesung von Kaliumjodid 3: sulfuric acid View Scheme

sulfuric acid

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