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Synthesis of 5-hydroxyquinolines

✍ Scribed by Jianke Li; Daniel W. Kung; David A. Griffith

Book ID
104097852
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
532 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

A series of 5-hydroxyquinolines has been prepared via the Skraup reaction. Several regioisomers were made either by selective displacement of a leaving group or by using a bromo substituent as a blocking group. The bromo group was found to be an excellent blocking group due to its stability during the Skraup reaction and easy removal thereafter. Halides at the 5-position of quinoline were found to be much more reactive than those at the 7-and 8-positions. Finally, we have also found a unique method to reduce the pyridyl ring on quinolines, leaving a halogen substituent untouched.

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