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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 9
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Original Articles

Survey of Solvents for the Conrad–Limpach Synthesis of 4-Hydroxyquinolones

, , &
Pages 1563-1569 | Received 21 Aug 2008, Published online: 02 Apr 2009
 

Abstract

A study of the synthesis of a 4-hydroxyquinoline derivative using the Conrad–Limpach reaction led to the identification of inexpensive and user-friendly solvents for this thermal condensation.

Notes

a A, methyl benzoate; B, ethyl benzoate; C, propyl benzoate; D, isobutyl benzoate; E, 2-nitrotoluene; F, 1,4-butanediol; G, tetrahydronaphthalene; H, decahydronaphthalene; I, 1,2,4-trichlorobenzene; J, Dowtherm A; K, 2,6-di-tert-butylphenol.

b Obtained from Lange's Handbook, 14th edition.

c Obtained from Aldrich catalog, 2007–2008 edition.

d Reaction with 1,4-butanediol did not produce any product.

e Reaction with decahydronaphthalene yielded only noncyclized enamine product.

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