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231225s2020 xx |||||o 00| ||eng c |
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|a 10.1002/mrc.4980
|2 doi
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|a pubmed24n1014.xml
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|a DE-627
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|a eng
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|a Vasconcelos Vontobel, Pedro Henrique
|e verfasserin
|4 aut
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|a Regioselective preparation and NMR spectroscopy study of 2-chloro-4-ethoxy-quinoline for the synthesis of 2-((3-aminopropyl)amino)quinolin-4(1H)-one
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|c 2020
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|a Text
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|2 rdacontent
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|a ƒaComputermedien
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|a ƒa Online-Ressource
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|a Date Completed 06.03.2020
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|a Date Revised 06.03.2020
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|a published: Print-Electronic
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|a Citation Status PubMed-not-MEDLINE
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|a © 2019 John Wiley & Sons, Ltd.
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|a Herein, we describe the C4-ethoxylation of 2,4-dichloroquinoline to prepare 2-chloro-4-ethoxy-quinoline (3), which is a prominent intermediate used for the synthesis of 2-substituted quinolones. To achieve this goal, we studied different conditions for the reaction between 2,4-dichloroquinoline and sodium ethoxide. We discovered that the use of 18-crown-6 ether as an additive and dimethylformamide as the reaction solvent allowed us to obtain the desired product 3 in very good yield and selectivity. In addition, a definitive distinction between the C2 and C4 ethoxylation products was achieved using 1 H─15 N heteronuclear multiple bond correlation. Compound 3 is an intermediate used for the synthesis of 2-((3-aminopropyl)amino)quinolin-4(1H)-one, which displays peculiar behavior during 1 H nuclear magnetic resonance analysis, such as the broadening of the H8 singlet and unexpected deuteration at the C8-position. Effort has been dedicated to understand these findings
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|a Journal Article
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|a Research Support, Non-U.S. Gov't
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|a 1H─15N HMBC
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|a H/D exchange
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|a NMR
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|a bederocin
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|a quinolines
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|a quinolones
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|a Dos Santos Fuscaldo, Rodrigo
|e verfasserin
|4 aut
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|a Dos Santos, Francisco Paulo
|e verfasserin
|4 aut
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|a Sobieski da Costa, Jessie
|e verfasserin
|4 aut
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|i Enthalten in
|t Magnetic resonance in chemistry : MRC
|d 1985
|g 58(2020), 4 vom: 30. Apr., Seite 295-304
|w (DE-627)NLM098179667
|x 1097-458X
|7 nnns
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| 773 |
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|g volume:58
|g year:2020
|g number:4
|g day:30
|g month:04
|g pages:295-304
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|u http://dx.doi.org/10.1002/mrc.4980
|3 Volltext
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