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A method for n-n coupling of secondary arylamines by electrochemical reaction

A technology of chemical reaction and secondary aromatic amine, which is applied in the field of N-N coupling of secondary aromatic amine by electrochemical reaction, which can solve the problems of unfriendly environment, small scope of application of substrates, expensive catalyst, etc., and achieve economic benefits and shorten reaction time , less restrictive effect

Active Publication Date: 2021-09-24
CHINA PHARM UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the deficiencies in the prior art, especially in the existing multi-substituted hydrazine compound synthesis methods, there are disadvantages such as the need for external chemical oxidants, alkali additives or transition metal catalysis, the scope of substrate application is small, the catalyst is expensive, and the environment is not friendly.

Method used

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  • A method for n-n coupling of secondary arylamines by electrochemical reaction
  • A method for n-n coupling of secondary arylamines by electrochemical reaction
  • A method for n-n coupling of secondary arylamines by electrochemical reaction

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Experimental program
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Effect test

Embodiment 1

[0045]

[0046] in such asFigure 8 Add 0.3mmol of N-methylaniline, 0.6mmol of sodium nitrite as electrolyte, 4.8mL of acetonitrile, 1.0mL of water and 1.2mL of ethanol in sequence to the 30mL electrolytic cell shown, and then put in a magnetic Stirrer, respectively add graphite carbon rod (Φ6mm), platinum sheet (1.0cm×1.0cm) as anode and cathode, turn on the power, adjust the current to 8.0mA, react at 450rpm, 50°C for 5 hours. After the reaction was completed, it was cooled to room temperature, the reaction solution was poured into 10 mL of water, extracted three times with ethyl acetate (10 mL), the organic phases were combined, and anhydrous Na 2 SO 4 Drying, concentration, separation by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane=1 / 8), the target product was obtained, and the yield was 80% of N-N coupled tetrasubstituted hydrazine compounds. figure 1 with figure 2 shown. 1 HNMR (400MHz, CDCl 3 )δ7.20–7.16(m,4H),6.80–6.71(m,6H),2.92...

Embodiment 2

[0048]

[0049] in such as Figure 8 Add 0.3mmol of N-methylbenzylamine, 0.6mmol of sodium nitrite as the electrolyte, 4.8mL of acetonitrile, 1.0mL of water and 1.2mL of ethanol in sequence to the 30mL electrolytic cell shown, and then add an appropriate size A magnetic stirrer was added with a graphite carbon rod (Φ6mm) and a platinum sheet (1.0cm×1.0cm) as the anode and cathode respectively. The power was turned on, the current was adjusted to 8.0mA, and the reaction was carried out at 450rpm and 50°C for 5 hours. After the reaction was completed, it was cooled to room temperature, the reaction solution was poured into 10 mL of water, extracted three times with ethyl acetate (10 mL), the organic phases were combined, and anhydrous Na 2 SO 4 Drying, concentration, silica gel chromatography column separation (developing solvent: ethyl acetate / n-hexane = 1 / 8) to obtain the target product, the yield of N-N coupled tetrasubstituted hydrazine compounds was 77%. image 3 with ...

Embodiment 3

[0051]

[0052] in such as Figure 8 Add 0.3mmol of diphenylamine, 0.6mmol of sodium nitrite as electrolyte, 4.8mL of acetonitrile, 1.0mL of water and 1.2mL of ethanol in sequence to the 30mL electrolytic cell shown, and then put in a magnetic stirrer of appropriate size, Add graphite carbon rods (Φ6mm) and platinum sheets (1.0cm×1.0cm) as anode and cathode respectively, turn on the power, adjust the current to 8.0mA, and react at 450rpm and 50°C for 5 hours. After the reaction was completed, it was cooled to room temperature, the reaction solution was poured into 10 mL of water, extracted three times with ethyl acetate (10 mL), the organic phases were combined, and anhydrous Na 2 SO 4 Drying, concentration, silica gel chromatography column separation (developing solvent: ethyl acetate / n-hexane = 1 / 8), to obtain the target product, the yield of 69% N-N coupled tetrasubstituted hydrazine compounds, NMR as shown in Figure 5 with Image 6 shown. 1 HNMR (400MHz, CDCl 3 )δ7...

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Abstract

The present invention relates to the technical field of organic synthesis, and discloses a method for realizing N-N coupling of secondary aromatic amines by means of an electrochemical reaction, that is, in a device equipped with an anode and a cathode, the N-methyl group shown in formula I Aniline analogues are used as raw materials, and electrolytes and solvents are added for electrolytic reaction to obtain tetrasubstituted hydrazine compounds as shown in formula II. The present invention adopts simple, cheap and easy-to-obtain starting materials. Compared with the prior art, under mild electrochemical conditions, the substrate undergoes anodic oxidation and cathodic reduction sequentially, and the single-component self-coupling of N-methylaniline compounds The multi-substituted hydrazine compounds were synthesized efficiently, avoiding the use of metal catalysis, strong base additives and strong oxidant oxidation, etc., and prepared important intermediate compounds more greenly.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for realizing N-N coupling of secondary aromatic amines through electrochemical reaction. Background technique [0002] N, N-multi-substituted hydrazine compounds are widely used as a very important chemical raw material and intermediate in organic synthesis and medicinal chemistry. In aerospace, it can be used as a rocket propellant, and in medicine, it can be used to synthesize new antibacterial drugs, antidiabetic drugs, anticancer drugs, anti HIV virus drugs, antihypertensive drugs, etc. In addition, it also has broad application prospects in chemical catalysts, synthetic pesticides, synthetic charge transport materials, dye industry, polymers and other fine chemical industries. In general, the direct oxidative coupling of two amine molecules is one of the most direct and atomic-step economical methods to form N–N bonds. So far, many methods have been dev...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/09C25B3/23C25B3/25C07C243/22C07C243/18
CPCC07C243/18C07C243/22
Inventor 杨照韩慧敏方正秦红王志祥
Owner CHINA PHARM UNIV
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