Sodium Carbonate → N-(2-methoxy-4-nitrophenyl)-N-(2-pyrid-2-ylethyl)amine

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5.62 g (0.03 mol) of 2-chloro-5-nitroanisole, 4 g (0.038 mol) of sodium carbonate, 4.5 g (0.037 mol) of 2-(2-ethylamino)pyridine, and 25 ml of NMP were introduced into a three-necked flask under nitrogen. The mixture was heated to 10° C. After reaction for 6 days, the reaction mixture was cooled and 75 ml of distilled water were then added slowly with vigorous stirring. The nitro derivative appeared in the form of a brown semi-solid, and was extracted with dichloromethane and then purified on a column of silica, eluting with 2/3 ethyl acetate/heptane. 2.1 g of expected nitro derivative (9) were obtained in the form of an orange solid. The proton NMR and 13C spectra and microanalyses were in accordance with the expected structure of the product.

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