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An investigation of the metabolic fate of the antimalarial drug, chlorguanide, NCp-chlorophenyl-NMsopropylbiguanide (1), was initiated in this laboratory in 1947 on the basis of previous studies (2) which indicated that this compound undergoes extensive degradation in the animal body. Interest in this problem was intensified by observations (3, 4) which suggested that the antimalarial activity of chlorguanide was due to a metabolite rather than to the parent drug.

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The introduction of an aldehyde group into certain aromatic nuclei by means of carbon monoxide, hydrogen chloride, and an appropriate catalyst is know as the Gatterman‐Koch reaction. The catalyst commonly used is aluminum chloride with cuprous chloride as a carrier. The carrier is not necessary when high pressure is used. Gatterman discovered the reaction when he tried to extend the Friedel‐Crafts reaction to the hypothetical formyl chloride.