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ChemicalBook CAS DataBase List 8-Quinolinecarbaldehyde
38707-70-9

8-Quinolinecarbaldehyde synthesis

11synthesis methods
8-Quinolinemethanol

16032-35-2

8-Quinolinecarbaldehyde

38707-70-9

General method: 8-quinoline methanol was dissolved in anhydrous DMSO (10 v/v), 1 equivalent of polymer bromide was added, and the reaction mixture was stirred at room temperature for the indicated time (see Table 1). Upon completion of the reaction, the mixture was filtered and the polymer bed was washed with DMSO. The DMSO layers were combined and the reaction was quenched with an ice-water mixture and subsequently extracted with ether. The ether layer was washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated to give pure 8-quinolinecarboxaldehyde. All products were structurally confirmed by nuclear magnetic resonance (NMR) and mass spectrometry (MS).

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Yield:38707-70-9 91%

Reaction Conditions:

with Br3(1-)*C10H15NPol(1+);dimethyl sulfoxide at 20; for 4 h;

Steps:

(i) Procedure for alcohols not containing acid-sensitive groups.
General procedure: To a mixture of alcohol in dry DMSO (10 volume) was added 1 equiv of polymer bromide and the reaction mixture was stirred at room temperature for a given period of time (Table 1). After the completion of the reaction, the reaction mixture was filtered and the polymer bed washed with DMSO. Combined DMSO layers were quenched with ice-water mixture and extracted with ether. The ether layer was given water wash, brine wash, dried over anhydrous sodium sulphate, and concentrated to get the pure carbonyl compounds. All the products were characterized by NMR and MS analysis.

References:

Prasanna;Mohanaraju [Tetrahedron Letters,2011,vol. 52,# 51,p. 6971 - 6973] Location in patent:experimental part

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