Chemistry Forum

EXAMPLE 1 N-(2-carbamoylethyl)-4-cyanopyridinium chloride Isolation of title compound
The following procedure was also applied to the preparation of the 3-cyanopyridine quaternization salt and also to mixtures of 3-cyano/4-cyanopyridine quaternization salts.
A five liter, three-necked round bottom flask was fitted with a mechanical stirrer, thermometer, dropping funnel and a beating mantle. The flask was charged with 637 g of 98% 4-cyanopyridine followed by one liter of isopropanol. Stirring was initiated and 426 g of acrylamide followed by another one liter portion of isopropanol was charged to the flask. The temperature was 6° C. at this point. The dropping funnel was charged with a solution of hydrogen chloride in isopropanol (21.12% w/v) and 1033 ml of this solution was added to the reaction flask over a one hour period. The reactor temperature was 46° C. at this point and a white precipitate had developed.


Heat was applied--the dropping funnel was replaced by a reflux condenser and the mixture which became thicker was refluxed for one hour, then allowed to cool overnight. The heavy precipitate was collected on a Buchner funnel by vacuum filtration. This was washed with cold isopropanol and dried in a vacuum oven for two hours at 60° C., affording 1172 g of the title compound with melting point 188°-189° C. Yield 92.6%.