5-Chloro-8-hydroxyquinoline synthesis
- Product Name:5-Chloro-8-hydroxyquinoline
- CAS Number:130-16-5
- Molecular formula:C9H6ClNO
- Molecular Weight:179.6
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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$19.00/5mg
130-16-5
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$5.00/5g
1198-14-7
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130-16-5
416 suppliers
$5.00/5g