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Improved Huang Minlon reaction

A reaction and solvent technology, applied in the improved Huang Minglong reaction field, can solve the problems of high equipment requirements, high energy consumption, high reaction temperature, etc., and achieve the effect of low energy consumption, low requirements, and easy large-scale industrial production

Active Publication Date: 2013-03-13
TIANJIN PHARMACN MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to solve the defects of high requirements on equipment and high energy consumption in Huang Minglong reaction due to high reaction temperature

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0014]

[0015] Add 165g of m-nitroacetophenone, 300mL of HMPA, and 320ml of 80% hydrazine hydrate into a 2L three-necked flask, and heat to 80°C for 1 hour. After cooling to 40°C, excess hydrazine hydrate and water are removed by water pump vacuum distillation, and the temperature in the bottle is controlled not to exceed 60°C. After completion, add 160 g of KOH, raise the temperature to 80 degrees, keep the temperature for 3 hours, cool down, pour into water, extract three times with dichloromethane, combine the organic phases, dry over anhydrous magnesium sulfate, and distill under reduced pressure to obtain 119 g of the product 3-ethylaniline , Yield: 98%.

[0016] Please do not add hydrogen spectrum and mass spectrum data.

Embodiment 2

[0018]

[0019] Add 257g of 4-nitro-1-naphthalenone, 500mL of HMPA, and 320ml of 80% hydrazine hydrate into a 2L three-necked flask, and heat to 80°C for 1 hour. After cooling to 40°C, excess hydrazine hydrate and water are removed by water pump vacuum distillation, and the temperature in the bottle is controlled not to exceed 60°C. After completion, add 160g of KOH, raise the temperature to 80°C, keep the reaction at this temperature for 3 hours, cool, pour into water, extract with dichloromethane three times, combine the organic phases, dry over anhydrous magnesium sulfate, and distill under reduced pressure to obtain the product 4-pentyl-1 -Naphthylamine 200g, yield: 93%.

[0020] Please do not add hydrogen spectrum and mass spectrum data.

Embodiment 3

[0022]

[0023] Add 260g of benzododecanone, 500mL of HMPA, and 320ml of 80% hydrazine hydrate into a 2L three-necked flask, and heat to 80°C for 1 hour. After cooling to 40°C, excess hydrazine hydrate and water are removed by water pump vacuum distillation, and the temperature in the bottle is controlled not to exceed 60°C. After completion, add 160g of KOH, raise the temperature to 80°C, keep the temperature for 3 hours, cool down, pour into water, extract with dichloromethane three times, combine the organic phases, dry over anhydrous magnesium sulfate, and distill under reduced pressure to obtain 236g of dodecylbenzene , Yield: 96%.

[0024] Please do not add hydrogen spectrum and mass spectrum data.

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Abstract

The invention discloses an improved Huang Minlon reaction, which adopts hexamethylphosphoramide as the solvent. By changing the reaction solvent, the reaction temperature is decreased from 200DEG C to 80DEG C, so that the reaction has lower equipment requirements and reduced energy consumption, and is easier for large-scale industrial production. At the same time test, tests find that the reaction not only can well reduce carbonyl compounds, but also can well reduce nitro-compounds and compounds containing nitro and carbonyl groups simultaneously.

Description

technical field [0001] The invention relates to a reduction reaction, in particular to an improved Huangminglong reaction. Background technique [0002] Huang Minglong's reduction method is an important reaction in organic chemistry, which can effectively reduce carbonyl compounds to alkyl compounds. In this method, the reaction substrate is usually mixed with hydrazine hydrate, ethylene glycol is used as a solvent, and heated to generate hydrazone compounds, and then potassium hydroxide is added to heat the reaction mixture to more than 200 degrees, and the corresponding alkyl compounds are obtained by pyrolysis. . Since the reaction is carried out under potassium hydroxide and high temperature, compounds that are sensitive to alkalinity and temperature are not suitable for this method. At the same time, in actual operation, the temperature as high as 200 degrees or more makes the method require high equipment in industrial production, and at the same time increases energ...

Claims

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Application Information

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IPC IPC(8): C07B31/00C07C211/45C07C211/58C07C209/68C07C209/36C07C15/107C07C5/02
Inventor 何磊田东奎
Owner TIANJIN PHARMACN MEDICAL TECH
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