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ChemicalBook CAS DataBase List Clopidol
2971-90-6

Clopidol synthesis

1synthesis methods
Ethyl acetoacetate

141-97-9

Clopidol

2971-90-6

The general procedure for the synthesis of 3,5-dichloro-2,6-dimethylpyridin-4-ol from ethyl acetoacetate is as follows: 130 g (1 mole) of ethyl acetoacetate, 39 g of styrene-DVB (D301T) resin, and 100 ml of distilled water were added sequentially to three 500 ml three-necked flasks. The reaction mixture was reacted under stirring for 30 hours, during which 85 g (5 moles) of ammonia gas was released. Subsequently, 142 g (2 moles) of chlorine gas was passed into the reaction system and the reaction was continued with stirring for 2 hours. The reaction temperature was maintained at 30°C. Upon completion of the reaction, the styrene-DVB (D301T) resin was removed by filtration, and the solid cake of the resin was washed with 100 mL of 10% aqueous sodium hydroxide. The styrene-DVB (D301T) resin was recycled. The filtrate was distilled to remove a small amount of ethanol and then left to crystallize. The crystallized product was filtered and dried to give 87.8 g of 3,5-dichloro-2,6-dimethylpyridin-4-ol in 91.5% yield.

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Yield:2971-90-6 91.5%

Reaction Conditions:

Stage #1:ethyl acetoacetate at 30; for 5 h;
Stage #2: with ammonium hydroxide at 10; for 2 h;
Stage #3: with chlorine at 30; for 2 h;Reagent/catalyst;Temperature;

Steps:

2 Example 2
In three 500 ml flask, 130 g of ethyl acetoacetate (1 mole), Styrene-DVB (D301T) 39 g resin, reaction at 30 5 hours, 100 ml of distilled water, stirring the ammonia released 85 g (5 mol), reacted at 10 deg.] C after 2 hours with stirring chlorine gas at 142 g (2 mol), reacted at 30 2 hours and filtered Styrene-DVB (D301 T) and the resin solid cake was washed with NaOH (10% concentration) was washed with an aqueous solution of 100 ml, Styrene-DVB (D301T) resin is recyclable. The filtrate was distilled to remove a small amount of ethanol, allowed to stand to crystallize, filtered and dried to give the desired product 87.8 g, 91.5% yield.

References:

Zhejiang University of Technology;Pei, Wen;Sun, Li;Zhao, Dianlin;Han, Yiting;Sun, Wen CN105753776, 2016, A Location in patent:Paragraph 0009; 0020; 0021

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