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A kind of synthetic method of heterocyclic compound 3-methoxypyridine

A technology of methoxypyridine and heterocyclic compound, which is applied in the synthesis field of heterocyclic compound 3-methoxypyridine, can solve the problems of unsuitability for industrial production, unobtainable raw materials, poor safety, etc., and achieves high conversion rate, high reaction Mild conditions and safe operation

Active Publication Date: 2019-01-11
ANHUI SCI & TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the above-mentioned synthetic method, highly toxic and complex compounds are used as catalysts, the cost is also high, the raw materials are not easy to obtain, and the safety is poor, so it is not suitable for industrial production

Method used

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  • A kind of synthetic method of heterocyclic compound 3-methoxypyridine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (1) Preparation of N-oxidized-3-fluoropyridine: 48.5g (0.5mol) 3-fluoropyridine, 170g, 30% (1.5mol) hydrogen peroxide, 120g (2mol) acetic acid were added to a 500mL three-necked flask respectively, and React under stirring conditions at 70°C for 8 hours, recover distilled water, recover acetic acid, add saturated sodium carbonate solution and stir to make the system alkaline, after distilled water, add chloroform to wash, filter to remove salt, recover chloroform, and vacuum distill to obtain 53.23 g, N-oxide-3-fluoropyridine, yield 94.21%.

[0022] (2) Preparation of N-oxidized-3-methoxypyridine: 56.5g (0.5mol) N-oxidized-3-fluoropyridine, 32.4g (0.6mol) sodium methylate, 3.75g (0.025mol) sodium iodide and 200mL of methanol were respectively added to a 500mL three-necked flask, and after stirring for 8 hours under reflux, methanol was recovered, neutralized to neutrality, water was distilled off, and 46.75g of N-oxide-3-methoxypyridine was obtained by rectification , ...

Embodiment 2

[0025] The preparation of N-oxidation-3-chloropyridine: 56.77g (0.5mol) 3-chloropyridine, 170.00g, 30% (1.5mol) hydrogen peroxide, 120.00g (2mol) acetic acid were added in the 500mL there-necked flask respectively, under stirring React at 70°C for 6 hours under the conditions, distill off water, recover acetic acid, add saturated sodium carbonate solution and stir to make the system alkaline, after distilling off water, add chloroform to wash, filter to remove salt, recover chloroform, and vacuum distill to obtain 61.58g. N-oxide-3-chloropyridine, yield 95.10%.

[0026] The second embodiment is the preferred embodiment

Embodiment 3

[0028] Preparation of N-oxidized-3-bromopyridine: 78.50g (0.5mol) 3-bromopyridine, 170.00g, 30% (1.5mol) hydrogen peroxide, 120.00g (2mol) acetic acid were added respectively in a 500mL three-necked flask, and stirred React at 70°C for 5 hours, distill off water, recover acetic acid, add saturated sodium carbonate solution and stir to make the system alkaline, after distilling off water, add chloroform to wash, filter to remove salt, recover chloroform, and vacuum distill to obtain 84.02g. N-oxide-3-bromopyridine, yield 96.57%.

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Abstract

The invention discloses a synthesis method of a heterocyclic compound 3-methoxypyridine. The method comprises the following steps: putting raw materials, i.e., 3-halogenated pyridine, hydrogen peroxide and acetic acid into a three-mouth flask, carrying out reaction for 4-8h at the temperature of 40-80 DEG C under the condition of stirring, recovering the acetic acid, adding a saturated sodium carbonate solution and stirring to enable a system to be alkaline, evaporating to remove water, then adding chloroform for washing, and carrying out vacuum distillation to obtain N-oxide-3-halogenated pyridine; respectively adding the N-oxide-3-halogenated pyridine, metal salt of alkyl alcohol, a catalyst A and alcohol into the three-mouth flask, carrying out reflux reaction for 5-8h under the condition of stirring, then cooling, neutralizing a product to be neutral, and carrying out distillation to obtain N-oxide-3-alkyloxypyridine; respectively adding the N-oxide-3-alkyloxypyridine, ferric trichloride, hydrazine hydrate, activated carbon and ethanol into the three-mouth flask, carrying out reaction at the temperature of 70 DEG C for 3h, cooling to room temperature, and carrying out vacuum distillation to obtain the 3-methoxypyridine. The synthesis method is high in intermediate conversion rate, mild in reaction conditions, safe in operation, low in price of raw materials and easy in raw material obtaining, thus being suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing heterocyclic compound 3-methoxypyridine. technical background [0002] With the rapid development of biomedicine and new pesticides, 3-methoxypyridine and its derivatives have been widely used as basic raw materials in the production of medicine, pesticides, food additives and other fields. [0003] There are two kinds of synthetic methods of 3-methoxypyridine and derivatives thereof reported at home and abroad at present, and a kind of is to be raw material reaction with 3-hydroxypyridine and methylating reagent or methyl alcohol; Another kind of method is to be 3- Synthesized from halogenated pyridine and sodium methoxide or methanol. [0004] For example, Shukla et al. reported in 2006 that 3-hydroxypyridine was used as a raw material to react with NaH in DMF to generate the corresponding sodium salt and then react with methyl iodide to obt...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/65
CPCC07D213/65
Inventor 张婷徐冬青陈俊明柏磊张雪梅
Owner ANHUI SCI & TECH UNIV