5-(Aminomethyl)-2-Furoic Acid

  • A. L. Mndzhoian


Ethyl 5-(Aminomethyl)-2-furoate. A mixture of 56.6 g (0.3 mole) of ethyl 5-(chloromethyl)-2-furoate having b.p. 112–114°/ /2 mm (see Vol. 1 of this work, p. 30), 46.2 g (0.33 mole) of hexamethylenetetramine, and 75 ml of dry chloroform was prepared in a two-liter four-necked round-bottomed flask fitted with a mercury-sealed stirrer and a reflux condenser protected by a calcium chloride tube. The continuously stirred mixture was boiled in a water bath for two hours. To the quaternary salt formed (Note 1) 380 ml of absolute alcohol was added, and heating and stirring were continued while hydrogen chloride (dried by passage through concentrated sulfuric acid) was passed in rapidly. When the mixture was saturated with hydrogen chloride, it was boiled for 1.5–2 hours. It was then allowed to cool to room temperature, the precipitated ammonium chloride was filtered off at the pump, and chloroform, alcohol, and volatile by-products were distilled from the filtrate completely, first at atmospheric and then at reduced pressure. When the residue in the distillation flask cooled, it solidified to a crystalline mass consisting mainly of the hydrochloride of ethyl 5-(aminomethyl)-2-furoate. The salt was treated with 180–200 ml of dry ether and then filtered off (Note 2).


Concentrate Sulfuric Acid Reflux Condenser Hydrogen Chloride Quaternary Salt Crystalline Mass 
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Literature Cited

  1. 1.
    O. Moldenhauer, W. Irion, and H. Marwitz, A. 583, 37 (1953).Google Scholar

Copyright information

© Springer Science+Business Media New York 1959

Authors and Affiliations

  • A. L. Mndzhoian

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