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A kind of preparation method and application of metal-organic three-membered cyclic compound

A cyclic compound and metal-organic technology, which is applied in the field of preparation of metal-organic ternary cyclic compounds, can solve the problems of mild reaction conditions, long reaction time and high production cost, and achieves stable chemical properties, easy mass synthesis, and good quality. The effect of reducing activity

Active Publication Date: 2022-03-18
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is also the use of expensive metal palladium and titanium as catalysts to catalyze primary amines and halides to prepare secondary amines, but the production cost is high and the reaction time is long
(2) Reductive amination method, by supporting noble metal catalysts (palladium carbon, platinum carbon) or using strong carcinogen Raney nickel to catalyze the reduction of Schiff base compounds into secondary amines, the reaction generally requires a high temperature and high pressure environment, and the reaction conditions are different. mild, dangerous
(3) The catalytic hydrogenation method of nitrile compounds requires the use of high-pressure hydrogen in the reaction process, and some also need to use strong alkali, which is more corrosive to the production equipment

Method used

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  • A kind of preparation method and application of metal-organic three-membered cyclic compound
  • A kind of preparation method and application of metal-organic three-membered cyclic compound
  • A kind of preparation method and application of metal-organic three-membered cyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]Step 1, 4-bromo-3-nitrotoluene (12.96g, 60mmol), pinacol diborate (18.29g, 72mmol) and potassium acetate (23.56g, 240mmol) were dissolved in 200mL dioxane, The mixture was stirred under argon atmosphere for 15 minutes. Then [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (2.20 g, 3 mmol) was added to the mixture, the reaction temperature was 85°C, stirred for 12 hours, and then cooled to 25°C; The reacted mixture was washed with 200 mL of CH 2 Cl 2 Extract to obtain an organic phase; then dry the organic phase with anhydrous sodium sulfate, vacuum filter, retain the filtrate, and spin to dry the solvent. Petroleum ether and dichloromethane with a volume ratio of 2:1 were passed through a silica gel column to obtain 10.02 g of yellow crystals, with a yield of 63.33%; 1 H-NMR (600MHz, DMSO-d 6 ,ppm)δ8.01(s,1H),7.63(d,J=7.40Hz,1H),7.51(d,J=7.40Hz,1H),2.44(s,3H),1.33(s,12H).

[0028] Step 2, weigh the yellow crystal (5g, 19mmol) obtained in step 1 and 2-bromo...

Embodiment 2

[0036] Will Co(NO 3 ) 2 ·6H 2 O (17.46mg, 0.06mmol) and the ligand H prepared in Example 1 2 Add DPD (33.57mg, 0.04mmol) into 12mL of a mixed solvent of methanol and acetonitrile with a volume ratio of 1:1.2, then put the mixture in an oven, first heat up for 1 hour, when the temperature rises to 82°C, keep it warm for 1 hour , and then cooled down to 33°C within 15 hours. After standing at room temperature for 6 days, a dark red solid precipitated on the bottle wall, and 24.31 mg of the target compound Co-DPD was obtained with a yield of 59.92%. ESI-MS mass spectrum: m / z: 896.5069[Co 3 (DPD) 3 ] 3+ .

Embodiment 3

[0038] Co(BF 4 ) 2 ·6H 2 O (20.44mg, 0.06mmol) and the ligand H prepared in Example 1 2 DPD (33.57mg, 0.04mmol) was added to 13mL of a mixed solvent of methanol and acetonitrile with a volume ratio of 1:0.9, and then the mixture was placed in an oven, and the temperature was raised for 1 hour. When the temperature rose to 80°C, it was kept for 1 hour. , and then cooled down to 28°C within 14 hours. After standing at room temperature for 1 week, a dark red solid precipitated on the bottle wall, and 22.80 mg of the target compound Co-DPD was obtained with a yield of 56.21%. ESI-MS mass spectrum: m / z: 896.5069[Co 3 (DPD) 3 ] 3+ .

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Abstract

The invention belongs to the technical field of fine chemicals, and relates to a preparation method and application of a metal-organic three-membered cyclic compound, wherein the preparation method uses L as a ligand and Co in a transition metal cobalt salt 2+ Metalorganic three-membered cyclic compounds were prepared as node reactions, and the synthetic route is as follows: L+Co 2+ →Co-L; The metal-organic three-membered ring compound prepared by the method of the present invention is novel in idea, has good reduction activity, stable chemical properties, and is easy to be synthesized in large quantities, so it is easier to put into practical application. Reaction of Co-DPD compound in reducing 4-[(4-methoxyphenyl)iminomethyl]benzoate to 4-[(4-methoxyphenyl)aminomethyl]benzoate , the yield can be as high as 83%, and it is used for the preparation of 4-[(4-methoxyphenyl)aminomethyl]benzonitrile and N-(4-methoxyphenyl)-4-(trifluoro The yields of methyl)-phenethylamine can be as high as 95% and 80%, respectively.

Description

technical field [0001] The invention relates to a preparation method and application of a metal-organic three-membered cyclic compound, belonging to the technical field of fine chemicals. Background technique [0002] Secondary amine compounds are one of the most important intermediates in fine chemical production. They can be used as intermediates in the rubber industry and cosmetics industry to manufacture vulcanization activators, plasticizers, softeners, and creams, etc.; in the synthetic dye industry It can be used to make rhodamine, acid violet, etc. Secondary amine compounds are also very important drug intermediates, which can be used to synthesize artesunate and oxaprozine. Artesunate is a good antimalarial drug that can quickly control the onset of malaria. Its mechanism of action is the same as that of artemisinin. It can be used in the rescue of cerebral malaria and various severe malaria. Oxaprozine is a non-steroidal anti-inflammatory drug, which can inhibit t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/576B01J31/24B01J31/22C07C253/30C07C255/43C07C213/00C07C217/84
Inventor 赵亮刘广洲魏建伟冀冠峰张宇段春迎
Owner DALIAN UNIV OF TECH
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