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Method for synthesizing TNPP and TAPP at high yield and high efficiency

A high-efficiency and high-yield technology, applied in organic chemistry and other directions, can solve the problems of difficult purification, difficult product separation, affecting product purity, etc., and achieve the effect of improving purity and yield.

Inactive Publication Date: 2017-08-18
NORTHWEST NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problem in this reaction process is that the product is difficult to separate, and because pyrrole is easy to self-polymerize, which affects the degree of reaction, the method is divided into two steps, which will affect the purity of the product. Therefore, this paper uses a simple and fast method. TNPP
Therefore, it is particularly important to explore the synthesis of TAPP as an intermediate. Although the synthesis of TAPP has been developed for a long time, there are still difficulties in the synthesis of high purity and high yield.
At present, the synthesis of TAPP is basically obtained through the ammoniation of TNPP, but due to the 2 The strong electron-withdrawing nature of the group makes nitroporphyrin synthesis low yield and difficult to purify

Method used

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  • Method for synthesizing TNPP and TAPP at high yield and high efficiency
  • Method for synthesizing TNPP and TAPP at high yield and high efficiency
  • Method for synthesizing TNPP and TAPP at high yield and high efficiency

Examples

Experimental program
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Effect test

Embodiment 1

[0032] The synthesis of embodiment 1, TNPP

[0033] Weigh 3.5g (23.23mmol) of p-nitrobenzaldehyde and 4.0ml (42.33mmol) of propionic anhydride, add them to 150ml of propionic acid under stirring, and heat the solution to 135°C;

[0034] Take 1.7ml (23.23mmol) freshly steamed pyrrole, dissolve it in 5ml propionic acid, then slowly add it dropwise to the above solution, stir and reflux for 40min to obtain a tar-like substance; cool, place for 24h, filter to obtain a black solid, wash with distilled water, and dry , the powder solid is TNPP crude product;

[0035] Add crude TNPP to 30ml of pyridine, heat to 110°C, reflux and stir for 1h, cool to room temperature, place in refrigerator (-4°C) for 10h, filter the tarry mixture, and wash the solid matter repeatedly with acetone and distilled water until no Then it is black, and 1.2-1.4 g of TNPP product is obtained, the purity is 86%, and the yield is 27-30%.

[0036] The elemental analysis of TNPP products is shown in Table 1; th...

Embodiment 2

[0037] The synthesis of embodiment 2, TAPP

[0038] Weigh 1.0 g of TNPP synthesized in Example 1, dissolve it in 50 ml of concentrated hydrochloric acid solution (concentration is 12 mol / l), react at room temperature for 1 h under nitrogen bubbling, and obtain TNPP solution;

[0039] Weigh 4.5g SnCl 2 ·H 2 O, dissolved in 60ml~70ml concentrated hydrochloric acid solution, added dropwise to the above TNPP solution under the protection of nitrogen, heated in a water bath to 75~80°C, and reacted for 30min; then use a cold water bath instead of a hot water bath to cool down to below 20°C;

[0040]Slowly add concentrated ammonia water (concentration 22% to 25%) into the above solution dropwise until pH = 8 to 9, then extract with chloroform for several times by Soxhlet extraction until the filtrate no longer turns black, collect the organic phase, and rotary evaporate The organic phase was dried, and finally dried under vacuum at 50° C. for 3 hours to obtain 0.7 g of purple solid...

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Abstract

The invention provides a method for synthesizing TNPP and TAPP at high yield and high efficiency and belongs to the technical field of chemical synthesis. The method provided by the invention is characterized in that a small amount of acetic anhydride or propionic anhydride is added to serve as a catalyst in the reaction process of nitrobenzaldehyde and pyrrole, so that the reaction speed is effectively improved and the reaction is performed rightwards to the maximum extent; hot pyrrole is adopted for dissolving and purifying the TNPP to obtain a TNPP product with high purity; in the process of synthesizing the TAPP, a strong reducer tin chloride is adopted for ammonifying the TNPP, and trichloromethane capable of dissolving the TAPP is adopted for efficiently separating the TAPP from an organic phase by adopting a Soxhlet extraction method, so that the purity and the yield of the TAPP are effectively improved.

Description

technical field [0001] The invention relates to a method for synthesizing functional material precursors TNPP and TAPP, in particular to a method for synthesizing TNPP and TAPP with high yield and high efficiency, and belongs to the technical field of chemical synthesis. Background technique [0002] Porphyrin is a kind of macromolecular heterocyclic compound formed by interconnecting the α-carbon atoms of four pyrrole subunits through methine bridges (=CH−). In nature, many porphyrins exist in the form of complexing with metal ions, such as chlorophyll containing the coordination structure of chlorin and metal magnesium and heme coordinating with metal iron. Porphyrin compounds are derivatives based on the porphine ring, and they all have very important physiological functions in organisms. In the porphine ring, each atom is basically on the same plane, forming a highly conjugated system with 11 conjugated double bonds that is easily affected by the electronic effect of th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 郭昊王婷杨武薛瑞石佩灵陈惠琴
Owner NORTHWEST NORMAL UNIVERSITY
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