2-Chloro-4-nitrotoluene → (E)-2-(2-chloro-4-nitrophenyl)-N,N-dimethylethenamine

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A reaction mixture of 8.49 g (48 mmol) of 2-chloro-4-nitrotoluene and 15.03 mL (72.8 mmol) of tert-butoxybis(dimethylamino)methane in 200 mL of THF is refluxed for 8 hours. The reaction solution is evaporated down and the residue is combined with petroleum ether. The precipitate is filtered off, rinsed with petroleum ether and dried at ambient temperature under a high vacuum. The product is used in other reactions without further purification. Yield: 11 g, C10H11ClN2O2 (M=226.66); calc.: molecular ion peak (M+H)+: 227/229; found: molecular ion peak (M+H)+: 227/229; Rf value: 0.55 (silica gel, petroleum ether/ethyl acetate (3:1)).

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