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Electrosynthesis of 5-amino-4-oxopentanoic acid hydrochloride

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Abstract

The electroreduction of methyl 5-nitro-4-oxopentanate was studied by means of a polarographic method and preparative electrolysis in acidic-alcoholic solutions. The effects of the following factors on the yield and quality of 5-amino-4-oxopentanoic acid hydrochloride were studied: the cathode material, amount of electricity, temperature, nature of the solvent, concentrations of the initial nitro compound and hydrochloric acid, and the cell design. It was shown by electrolysis at a controlled potential and in a galvanostatic mode that the products of methyl 5-nitro-4-oxopentanate electroreduction are hydroxyamino and amino compounds, and also ammonium chloride, nitromethane, methylhydroxylamine hydrochloride, and monomethylamine hydrochloride. Their ratio depends on the electrolysis conditions. The highest overall substance yield (61.1–66.0%) and current yield (68.1–68.6%) of 5-amino-4-oxopentanoic acid hydrochloride was achieved at a copper cathode in a filter-press cell. The content of the main substance in the electrochemically obtained samples of 5-amino-4-oxopentanoic acid was 89.5–91.0%.

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Authors and Affiliations

  1. Federal State Unitary Enterprise “State Scientific Center NIOPIK”, Moscow, Russia

    A. A. Konarev, E. A. Lukyanets & V. M. Negrimovskii

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  1. A. A. Konarev
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  2. E. A. Lukyanets
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  3. V. M. Negrimovskii
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Correspondence to A. A. Konarev.

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Original Russian Text © A.A. Konarev, E.A. Lukyanets, V.M. Negrimovskii, 2007, published in Elektrokhimiya, 2007, Vol. 43, No. 11, pp. 1357–1365.

The paper is published based on the materials presented at the 16th All-Russian Meeting on Electrochemistry of Organic Compounds, Novocherkassk (EKhOS-2006).

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Konarev, A.A., Lukyanets, E.A. & Negrimovskii, V.M. Electrosynthesis of 5-amino-4-oxopentanoic acid hydrochloride. Russ J Electrochem 43, 1252–1259 (2007). https://doi.org/10.1134/S1023193507110067

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  • DOI: https://doi.org/10.1134/S1023193507110067

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