2-amino quinoline
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| Surname | 2-amino quinoline | ||||||||||||||||||
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| Molecular formula | C 9 H 8 N 2 | ||||||||||||||||||
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| properties | |||||||||||||||||||
| Molar mass | 144.18 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
136 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
2-Aminoquinoline is a heterocyclic chemical compound which consists of a quinoline skeleton with an amino group in the 2-position .
presentation
2-Aminoquinoline can be made by amination of quinoline. Many nucleophilic aromatic substitutions occur on quinoline, preferably on the electron-deficient 2-position of the pyridine ring . This includes the amination by a Chichibabin reaction , in which by use of potassium amide as nucleophile in liquid ammonia at -66 ° C the amide ion preferably to the 2-position of quinoline is added . Subsequent oxidation with potassium permanganate can release 2-aminoquinoline. This is the kinetic reaction product. When the reaction temperature is increased to −40 ° C, isomerization to the thermodynamically more stable 4-substituted product takes place.
Individual evidence
- ↑ a b c data sheet 2-Aminoquinoline from Sigma-Aldrich , accessed on May 12, 2011 ( PDF ).
- ↑ JA Joules, K. Mills: Heterocyclic Chemistry , 5th Edition, pp. 177-199, Blackwell Publishing, Chichester, 2010, ISBN 978-1-4051-9365-8 .
- ↑ H van der Plas: Oxidative Amino-Dehydrogenation of Azines , in: Adv. Heterocycl. Chem. 2004 , 86 , 1-40.
- ↑ JA Zoltewicz, LS Helmick, TM Oestreich, RW King, PE Kandetzki: Addition of amide ion to isoquinoline and quinoline in liquid ammonia. Nuclear magnetic resonance spectra of anionic σ-complexes , in: J. Org. Chem. 1973 , 38 , 1947-1949; doi : 10.1021 / jo00950a036 .