ChemicalBook CAS DataBase List 3-Picolyl chloride hydrochloride

3-Picolyl chloride hydrochloride synthesis

4synthesis methods

Product Name:3-Picolyl chloride hydrochloride
CAS Number:6959-48-4
Molecular formula:C6H7Cl2N
Molecular Weight:164.03

Chloromethyl pyridine hydrochloride is the important industrial chemicals of various agricultural chemicals, medicine intermediate, Insecticides (tech) & Herbicides (tech), sterilant. A synthetic method of 3-(chloromethyl)pyridine hydrochloride (also known as 3-Picolyl chloride hydrochloride) comprises steps as follows: (1) 3-methylpyridine is taken as a raw material, water is taken as a solvent, and the 3-methylpyridine is oxidized into 3-picolinic acid with potassium permanganate, wherein the molar ratio of the 3-methylpyridine to the potassium permanganate is 1:(2.1-2.3), the oxidizing temperature is kept at 85-90 DEG C, heating is performed for 30 min, a reaction solution is adjusted to be acid after the reaction, and 3-picolinic acid is obtained after cooling and filtration; (2) the 3-picolinic acid and methanol react to produce methyl pyridine-3-carboxylate under the acid condition, and the molar ratio of the 3-picolinic acid to the methanol is 1:1.3; (3) the methyl pyridine-3-carboxylate is reduced to 3-pyridinemethanol; (4) the 3-pyridinemethanol reacts with thionyl chloride to produce a target product, namely, 3-(chloromethyl)pyridine hydrochloride, and the molar ratio of the 3-pyridinemethanol to the thionyl chloride is 1:(1.1-1.3).

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6959-48-4
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Yield:6959-48-4 93.26%

Reaction Conditions:

Stage #1:3-Methylpyridine with hydrogenchloride at 0; under 760.051 Torr; for 9 h;Large scale;
Stage #2: with chlorine at 110 - 125; for 8 h;Large scale;Temperature;

Steps:

3 Example 3
A 1000 mL four-neck bottle was placed in an ice water bath.Add 500g (content 99.5%,After the moisture content of 0.02%) 3-methylpyridine,Turn on the agitation,The dry hydrogen chloride gas (85g/h) is introduced under normal pressure.Water bath temperature control 0 ° C,Reacting in a dry anhydrous state,After all the white solid hydrochloride is formed,Stop stirring and continue to pass hydrogen chloride gas.The solid begins to dissolve,After introducing hydrogen chloride gas for 9 hours, 1265 g of liquid 3-methylpyridine hydrochloride was obtained (quantitative 3-methylpyridine content was39.53%).Transfer the above hydrochloride to a 2000 mL four-necked flask and place in an oil bath.After the stirring is started and the temperature is raised to 125 ° C, the chlorine gas after drying is started.Ventilation speed 50g/h,After 8h, the gas phase detection result was 3-methylpyridine: 3-chloromethylpyridine = 45:52 (gas phase qualitative ratio),Stop the chlorine and cool down to 110 ° C, at this temperature,Distilled under reduced pressure at a pressure of -0.08 MPa,A total of 236 g of distillate was obtained.Is unreacted 3-methylpyridine,The quantitative 3-methylpyridine content is 98.2%;The remaining bottom material is a light yellow solid.3-chloromethylpyridine hydrochloride,A total of 459.9g,The quantitative 3-chloromethylpyridine content is 73.88%,The yield was calculated to be 93.26%.

References:

Nanjing Hong Sun Biochemical Co., Ltd.;Nanjing Hong Sun Co., Ltd.;Zhan Xinhua;Zhong Jingsong;Wang Fujun;Chen Honglong;Mu Dengyou;Yang Cheng CN108409641, 2018, A Location in patent:Paragraph 0020; 0021; 0023; 0024; 0025; 0026; 0027

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