Sodium Carbonate → 2-(Chloromethyl)quinoline

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Reaction Steps

Monomer IV can be obtained by following this general procedure: A mixture of 2-(chloromethyl)quinoline·HCl and a 1% sodium carbonate solution is added to a separatory funnel, and extracted with methylene chloride. The methylene chloride extracts are passed through a cone of anhydrous sodium sulfate, and collected in a flask. 2-(Chloromethyl)quinoline is obtained in the flask after evaporation of the methylene chloride. To the flask containing 2-(chloromethyl)quinoline, is added MEHQ and acetone. The mixture is heated to about 56° C. DMAPMA is added to the solution. The resulting mixture is heated for about 110 min at 56° C., then cooled to about 25° C. for 2 hrs. The resulting white solid, the quaternary ammonium salt of DMAPMA and 2-(chloromethyl)quinoline is isolated by filtration.

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