Toluene → Benzamide, 3-bromo-5-chloro-2,6-dimethoxy-N-(1-ethyl-2-pyrrolidinylmethyl)-

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Reaction Steps

20 ml of thionyl chloride is added to 11.82 g (0.04 mol) of 3-bromo-5-chloro-2,6-dimethoxybenzoic acid. The mixture is heated on a steam bath for 1 hour. To the solution is added 50 ml of toluene. The solvent and excess thionyl chloride is evaporated at reduced pressure. The residue is dissolved in 50 ml of dry methyl ethyl ketone. The solution is added dropwise while stirring to 5.13 g (0.04 mol) 2-(aminomethyl)-1-ethylpyrrolidine in 50 ml methyl ethyl ketone. After stirring for 30 minutes at room temperature 300 ml of ether is added. The obtained semisolid product is separated and dissolved in 300 ml of water. Sodium hydroxide solution is added while stirring and cooling in ice. The precipitate is collected and washed with water. Yield: 12.0 g, m.p. 124°-25° C.

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