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Reduction of 3-substituted 2-methylquinolines with sodium tetrahydroborate

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Reduction of esters of 2-metylquinoline-3-carboxylic acids and their perchlorates gave esters of 1,4-dihydro-2-methylquinoline-3-carboxylates, while derivatives of 1,2-dihydroquinoline were formed in the case of 1,2-dimethyl-3-ethoxycarbonyl-7-methoxyquinolinium perchlorate. Reduction of esters of 2-methylquinoline-3-carboxylic acid, 1,2-dimethyl-3-ethoxycarbonyl-1-methoxyquinolinium perchlorate and 3-acetyl-2-methyl-quinoline with sodium tetrahydroborate in acetic acid gave esters of 1,2-dimethyl- and 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylic acid and 3-acetyl-2-methyl-1,2,3,4-tetrahydroquinoline.

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Authors
  1. A. Sobolev
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  2. B. Vigante
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  3. Ya. Ozols
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  4. G. Duburs
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Additional information

Latvian Institute of Organic Synthesis, Riga, LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1383–1390, October, 1996. Original article submitted October 11, 1995.

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Sobolev, A., Vigante, B., Ozols, Y. et al. Reduction of 3-substituted 2-methylquinolines with sodium tetrahydroborate. Chem Heterocycl Compd 32, 1189–1195 (1996). https://doi.org/10.1007/BF01169232

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