Abstract
Epichlorohydrin reacts with diphenylamine in the presence of acetic acid to give N-(γ-chloro-β-hydroxypropyl)diphenylamine, cyclized to N-phenyl-1, 2, 3, 4-tetrahydro-3-hydroxyquinoline; a study is also made of its conversion to N-(γ-diphenylamine-β-hydroxypropyl)pyridinium chloride, N-(γ-amino-β-hydroxypropyl)diphenylamine, (γ-diphenylamino-β-hydroxybutyronitrile, and N-(β, γ-epoxypropyl)diphenylamine, the latter on treatment with hydrogen chloride giving back the starting N-(γ-chloro-β-hydroxypropyldiphenylamine. It is shown that when γ-diphenylamino-β-hydroxybutyronitrile is heated in alkali, the products are the salt of γ-diphenylamino-β-hydroxybutyric acid and diphenylamine, i.e. a nitrogen-carbon bond is broken.
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References
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For Part I see [3].
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Kutkevichus, S.I., Vorozhtsov, N.N. Investigation of the products of reaction of epichlorohydrin with aromatic amines. Chem Heterocycl Compd 1, 368–371 (1966). https://doi.org/10.1007/BF00473811
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DOI: https://doi.org/10.1007/BF00473811