5-Chloro-8-hydroxyquinoline synthesis
- Product Name:5-Chloro-8-hydroxyquinoline
- CAS Number:130-16-5
- Molecular formula:C9H6ClNO
- Molecular Weight:179.6
3054-95-3
95-85-2
130-16-5
GENERAL PROCEDURE: A 1N HCl solution (82.5 mL) was added to a round-bottomed flask containing 4-chloro-2-aminophenol (~1 mmol). Acrolein diethyl acetal (2.5 mmol) was added to the reaction mixture. The resulting solution was refluxed at 111°C for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and neutralized to pH 7-8 with solid Na2CO3. Subsequently, the product was extracted with dichloromethane (3 x 100 mL), the organic layers were combined and dried with anhydrous Na2SO4. After removal of solvent by evaporation under reduced pressure, the crude product was purified by column chromatography with the eluent being a mixture of 15% ethyl acetate/cyclohexane and methanol to afford the target compound 5-chloro-8-hydroxyquinoline.
Yield:130-16-5 49%
Reaction Conditions:
with hydrogenchloride in water at 111; for 24 h;Doebner-von Miller Reaction;
Steps:
GENERAL EXPERIMENTAL PROCEDURE FOR CYCLIZATION OF ANILINESTO QUINOLINE
General procedure: A 1N HCl solution (82.5 mL) was added to the aniline (~1 mmol) in a round bottom flask. To this was added acrolein diethyl acetal (2.5 mmol). The resulting solution was refluxed at 111 °C for 24 hours. After cooling to room temperature, the solution was neutralized (pH 7-8) by addition of solid Na2CO3. The product was then extracted into dichloromethane (3 x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was then purified by column chromatography (elution mixture of hexane with ethyl acetate or 15% ethyl acetate/cyclohexane with methanol) to give the desired quinoline product.
References:
Ramann, Ginelle A.;Cowen, Bryan J. [Tetrahedron Letters,2015,vol. 56,# 46,p. 6436 - 6439] Location in patent:supporting information
130-26-7
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130-16-5
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$5.00/5g
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130-16-5
428 suppliers
$5.00/5g