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Synthetic method of 3-methyl indole

A technology of methyl indole and synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of complex reaction process, large toxic reagent, high price, etc., and achieve the effect of simple process, safe reaction reagent, and industrialized production

Inactive Publication Date: 2012-05-02
太仓市运通化工厂
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many main synthetic methods of 3-methylindole, but most of them are difficult to realize industrialization due to the use of a large amount of toxic reagents, complex reaction process, high price and low yield.

Method used

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  • Synthetic method of 3-methyl indole
  • Synthetic method of 3-methyl indole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 96.8g of o-ethylaniline and 40.3g of formic acid aqueous solution with a volume fraction of 90% in a 250mL three-necked flask, heat to reflux for 3h, then place the reaction system overnight, evaporate the solvent under reduced pressure, then add 35mL of toluene and heat to dissolve. Cool to 10°C for crystallization for 6 hours, and filter with suction to obtain 105 g of N-formyl o-ethylaniline, m.p: 59-61°C, yield 89%.

[0015] Add 36g KOH and 100mL toluene into a 500mL three-necked flask and heat to reflux, slowly add a solution consisting of 72g N-formyl o-ethylaniline and 50mL toluene, dropwise for 3h, react for 2h after the dropwise addition, and then heat up and steam out Solvent until the temperature in the bottle reaches 320°C, then cool down naturally, add 50mL*3 water, stir and wash, dry to obtain 50.5g of 3-methylindole, m.p: 95-97°C, yield 80%.

Embodiment 2

[0017] Add 64.5g of o-ethylaniline and 32.3g of formic acid aqueous solution with a volume fraction of 90% in a 250mL three-necked flask, heat to reflux for 2h, then place the reaction system overnight, evaporate the solvent under reduced pressure, then add 25mL of toluene and heat to dissolve. Cool to 10°C and crystallize for 7 hours, filter with suction to obtain 70 g of N-formyl o-ethylaniline, m.p: 59-61°C, yield volume fraction 90%.

[0018] Add 24g KOH and 80mL toluene into a 500mL three-necked flask and heat it to reflux, slowly add a solution consisting of 48g N-formyl o-ethylaniline and 30mL toluene, dropwise for 2h, react for 2h after the dropwise addition, and then heat up and steam out Solvent until the temperature in the bottle reaches 320°C, then cool down naturally, add 50mL*3 water, stir and wash, dry to obtain 35 grams of 3-methylindole, m.p: 95-97°C, yield 81%.

Embodiment 3

[0020] Add 174g of o-ethylaniline and 58.1g of formic acid aqueous solution with a volume fraction of 90% in a 500mL three-necked flask, heat to reflux for 4 hours, then place the reaction system overnight, evaporate the solvent under reduced pressure, then add 50mL of toluene to dissolve, cool Crystallize at 10°C for 8 hours, and filter with suction to obtain 180 g of N-formyl o-ethylaniline, m.p: 59-61°C, yield 89%.

[0021] Add 43g KOH and 150mL toluene into a 500mL three-necked flask and heat to reflux, then slowly add a solution consisting of 129g N-formyl o-ethylaniline and 90mL toluene, the time for the dropwise addition is 4h, after the dropwise addition, react for 3h, then heat up and steam out Solvent until the temperature in the bottle reaches 320°C, then cool down naturally, add 100mL*3 water, stir and wash, dry to obtain 110g of 3-methylindole, m.p: 95-97°C, yield 82%.

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Abstract

The invention discloses a synthetic method of 3-methyl indole. The method comprises the following steps of: adding o-ethylaniline and 90 percent by volume of formic acid aqueous solution into a first reactor (A), heating to undergo a reflux reaction for 2-4 hours, standing a reaction system overnight, evaporating a solvent to dryness under reduced pressure, adding toluene, heating, dissolving, cooling to 10 DEG C, devitrifying for 6-8 hours, and performing suction filtration to obtain N-formoxyl o-ethylaniline; and adding potassium hydroxide and toluene into a second reactor (B), heating for refluxing, dropwise adding a toluene solution of N-formoxyl o-ethylaniline slowly within four 4 hours, heating to undergo a reflux reaction for 2-3 hours, raising the temperature for evaporating a solvent out till the temperature is 320 DEG C, naturally cooling, washing with water, and drying to obtain 3-methyl indole. The synthetic method of 3-methyl indole disclosed by the invention has the advantages of safe reaction reagent, simple process, small quantity of steps, high yield and easiness for realizing industrial production.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a method for synthesizing 3-methylindole. Background technique [0002] 3-Methylindole is an important pharmaceutical and pesticide intermediate. Due to its unique chemical structure, many active pharmaceutical and pesticide products can be derived, and it has an extremely broad market demand prospect. At present, there are many main synthetic methods of 3-methylindole, but most of them are difficult to realize industrialization due to the use of a large amount of toxic reagents, complex reaction process, high price and low yield. Contents of the invention [0003] The present invention is just to overcome the above disadvantages, and the technical problem to be solved is to provide a synthetic method of 3-methylindole which is safe in reagents, simple in process, high in yield and easy to realize industrialized production. [0004] In order to solve the problems of...

Claims

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Application Information

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IPC IPC(8): C07D209/08
Inventor 张卫东
Owner 太仓市运通化工厂
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