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ChemicalBook CAS DataBase List Pymetrozine
123312-89-0

Pymetrozine synthesis

2synthesis methods
Pymetrozine is commercially produced via a multi-step process starting from nicotinic acid, which is converted to 3-pyridinecarboxaldehyde through reduction (e.g., via Rosenmund or DIBAL-H) or from 3-picoline via oxidation and selective reduction. This aldehyde undergoes condensation with hydrazine hydrate in ethanol to form the hydrazone, which is then cyclised with triazine precursor 3-amino-1,2,4-triazine under acidic conditions to construct the 1,2,4-triazolo[1,5-a]pyridine core. Final N-methylation using dimethyl sulphate or methyl iodide with potassium carbonate in DMF yields pymetrozine.
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Yield:123312-89-0 2080 g

Reaction Conditions:

in methanol at 65; for 12 h;Green chemistry;Large scale;Temperature;

Steps:

1.5 Example 1 Preparation of pymetrozine

(5) Preparation of pymetrozine: 5000ml three-necked flask into methanol (solvent) 1000ml, acetamidotriazinone1700g, 98wt% concentrated sulfuric acid 15g, stirring conditions, dropping saturated hydrogen chloride methanol solution 1100g, control the drop temperature40 , dropping time 2h, dropping finished to keep the temperature at 65 , holding 4h.Adjust the pH to 8, and then add 1070g of niacin, control the drop temperature at 65 , dropping time 3h, dropping finished to keep the temperature at 65 , the reaction 12h. Crystallization from 0 to -5 ° CHeart and dried to obtain 2080g of pymetrozine, the yield of 96%, recovery of by-product methyl acetate 740g, can be used for the synthesis of acetylHydrazine.

References:

CN103724327,2017,B Location in patent:Paragraph 0014; 0030; 0035; 0040-0042; 0043-0045; 0046-0048

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