ChemicalBook CAS DataBase List 4-Chloro-6-fluoroquinoline

4-Chloro-6-fluoroquinoline synthesis

6synthesis methods

Product Name:4-Chloro-6-fluoroquinoline
CAS Number:391-77-5
Molecular formula:C9H5ClFN
Molecular Weight:181.59

38470-26-7

391-77-5

General procedure for the synthesis of 4-chloro-6-fluoroquinoline from 6-fluoro-2,3-dihydroquinolin-4(1H)-one: 412.55 mL of phosphoryl chloride, 11.5 g of iodine, and 165.0 g of manganese dioxide were added to a four-necked flask fitted with a stirrer and heated under stirring to 50 °C. Subsequently, 660 mL of a dichloroethane solution containing 165.02 g of 6-fluoro-2,3-dihydroquinolin-4(1H)-one was slowly added dropwise. After completion of the dropwise addition, the reaction mixture was refluxed for 2 hours. After completion of the reaction, the dichloroethane solvent was removed by distillation under reduced pressure. The residue was neutralized to pH 5-6 with cold aqueous sodium bicarbonate and filtered. The filter cake was washed with water to neutral and finally dried under vacuum to give 154.22 g of light gray solid 4-chloro-6-fluoroquinoline in 85.0% yield.

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391-77-5
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Yield:391-77-5 85%

Reaction Conditions:

with manganese(IV) oxide;iodine;trichlorophosphate in 1,2-dichloro-ethane at 50; for 2 h;Reagent/catalyst;

Steps:

6 Example 6
This example is a process for the preparation of 4-chloro-6-fluoroquinoline.

A four-necked flask was charged with 412.55 mL of phosphorus oxychloride,11.5 g of iodine and 165.0 g of manganese dioxide,Heated to 50 ° C with stirring,660 mL of a dichloroethane solution containing 165.02 g of 6-fluoro-2,3-dihydroquinolin-4 (1H) -one prepared in Example 4 was added dropwise,Reflux reaction 2h,The dichloroethane was then removed in vacuo,The residue was neutralized with cold aqueous sodium bicarbonate to a pH of 5 to 6, filtered and the filter cake was washed with water to neutral,Dried in vacuo to give 154.22 g of a pale gray solid 4-chloro-6-fluoroquinoline in a yield of 85.0%.

References:

CN106565602,2017,A Location in patent:Paragraph 0008; 0024; 0025; 0026; 0027

391-78-6 Synthesis