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Transformations of 2-Ethyl-2-methyl-2,3-dihydro-1H-indole at the 3-Position

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Abstract

The oxidation of N-acetyl-2-ethyl-2-methyl-2,3-dihydro-1H-indole with pyridinium chlorochromate, CrO3 · 2 Py, or CrO3 gave N-acetyl-2-ethyl-2-methyl-2,3-dihydro-1H-indol-3-one which was hydrolyzed to 2-ethyl-2-methyl-2,3-dihydro-1H-indol-3-one. The latter was reduced with sodium tetrahydridoborate in ethanol to 3-hydroxy derivative and converted to the corresponding oxime by treatment with hydroxylamine hydrochloride in methanol. Baeyer—Villiger oxidation of 2-ethyl-2-methyl-2,3-dihydro-1H-indol-3-one and Beckmann rearrangement of its oxime were studied.

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Acknowledgments

The analytical data were obtained using the equipment of the Chemistry joint center (Ufa Institute of Chemistry, Russian Academy of Sciences).

Funding

This study was performed in the framework of state assignment (project nos. AAAA-A19-119020890014-7, AAAA-A17-117011910027-0.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, 450054, Russia

    L. R. Latypova, Sh. M. Salikhov, A. G. Mustafin & I. B. Abdrakhmanov

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  1. L. R. Latypova
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  2. Sh. M. Salikhov
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  3. A. G. Mustafin
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  4. I. B. Abdrakhmanov
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Corresponding author

Correspondence to Sh. M. Salikhov.

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The authors declare the absence of conflict of interest.

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Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 1, pp. 97–102.

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Latypova, L.R., Salikhov, S.M., Mustafin, A.G. et al. Transformations of 2-Ethyl-2-methyl-2,3-dihydro-1H-indole at the 3-Position. Russ J Org Chem 56, 76–81 (2020). https://doi.org/10.1134/S1070428020010133

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  • DOI: https://doi.org/10.1134/S1070428020010133

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