Synthesis of 5-cyano-1-hydrocarbylpyrrole-2-acetic acid

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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26032647, C07D20734

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042461758

ABSTRACT:
When reacting a 2,2,2-trichloro-1-(N-hydrocarbylpyrryl-2)-ethanol in solution with a cyanating reagent under basic conditions, advantages are achieved by performing the reaction in an aqueous reaction medium containing at least 3 equivalents of calcium hydroxide per mole of the 2,2,2-trichloro-1-(N-hydrocarbylpyrryl-2)-ethanol used in the reaction. Good yields are achieved in short reaction times. Large excesses of cyanating reagents are not required. It is unnecessary to add components to the reaction vessel on a periodic basis in order to achieve good yields. And it is possible to isolate the desired product in the form of a calcium salt by a facile procedure. This enables the desired product to be formed by acidification of the isolated calcium salt without the hazards of toxic HCN generation.

REFERENCES:
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patent: 3755307 (1973-08-01), Carson
patent: 3803169 (1974-04-01), Carson
patent: 3803171 (1974-04-01), Carson
patent: 4048191 (1977-09-01), Carson
Wong et al., The Journal of Pharmacology, vol. 185, pp. 127-138 (1973).
Blinn et al., J. Amer. Chem. Soc. 76, pp. 37-39 (1954).

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