N,N-dimethyl-aniline T=230°C;

1: 100 percent / K2CO3 / acetone / 18 h / Heating 2: 24 h / 180 °C View Scheme

T=220°C; in vacuo; Yield given. Yields of byproduct given;

1: potassium carbonate 2: decalin / Reflux View Scheme

1: 2: in decalin Claisen Rearrangement;

1.1: potassium carbonate / acetone / 4 h / 40 °C 2.1: triethylamine; zinc trifluoromethanesulfonate; (1S,2R)-(+)-N-methylephedrine / toluene / 20 °C 2.2: 16 h / 20 °C 3.1: 4-(N,N-dimethlyamino)pyridine; 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere 4.1: ethylene glycol dimethyl ether / 6.5 h / 20 - 65 °C / Inert atmosphere 5.1: potassium carbonate; hydrogen / palladium on activated charcoal / water; methanol / 16 h / 20 °C 6.1: sodium hydroxide / water; methanol / 0.5 h / -5 °C 6.2: 18 h / -5 - 20 °C 6.3: pH 2 - 3 View Scheme

2.1: palladium dichloride; copper dichloride; oxygen / tetrahydrofuran; methanol / 10 h / 20 °C 2.2: 5 h / 20 °C View Scheme

sodium hydride

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