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Method for compounding amino-substituted arylate compound

A synthesis method and compound technology, which are applied in the synthesis of aryl ester compounds and the synthesis of amino-substituted aryl ester compounds, can solve the problems of low yield, selectivity still needs to be further improved, and limit the possibility of larger-scale application. Achieve the effect of avoiding the use of precious metals and good industrialization prospects

Active Publication Date: 2013-12-04
JIAXING NIYA OPTOELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the disadvantage lies in the use of expensive noble metal palladium and specific structure of phosphine ligands, which limits its larger-scale application.
[0011] As mentioned above, although a variety of methods for the synthesis of amino-substituted aryl ester compounds have been disclosed in the prior art, there are some defects in these methods, such as the use of expensive reagents, low yield, selectivity still needs to be further improved, etc. , which limits the practical application of these methods, and cannot meet the current urgent demand for the synthesis of such compounds

Method used

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  • Method for compounding amino-substituted arylate compound
  • Method for compounding amino-substituted arylate compound
  • Method for compounding amino-substituted arylate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: the synthesis of phenyl anthranilate

[0061]

[0062] In a dry and clean reactor, add 50ml solvent THF, then add the above formula (II) compound, formula (III) compound, formula (a) copper compound and 1,10-phenanthroline in sequence, so that the molar ratio is 1 :1:0.05:0.1, wherein the compound of formula (II) is 10mmol, and the reaction system is stirred and reacted at 40°C for 15 hours.

[0063] After the reaction was finished, filter, and the filtrate was rotary evaporated with a rotary evaporator to remove the solvent, and the residue was purified by 200-300 mesh silica gel column chromatography to obtain the target product as a solid, with a yield of 99.4% and a purity of 99.1% ( HPLC).

[0064] Melting point: 70-71°C;

[0065] NMR: 1 H NMR (500MHz, CDCl 3 )δ5.76(s,2H),6.67-6.72(m,2H),7.14-7.20(m,2H),7.27-7.29(m,1H),7.30-7.35(m,1H),7.39-7.45( tm,2H), 8.07-8.10(m,1H).

Embodiment 2

[0066] Embodiment 2: the synthesis of m-methylphenyl anthranilic acid

[0067]

[0068] In a dry and clean reactor, add 50ml of solvent acetone, then add the above formula (II) compound, formula (III) compound, formula (b) copper compound and 1,10-phenanthroline monohydrate successively to make the mole The ratio is 1:1.5:0.1:0.2, wherein the compound of formula (II) is 10 mmol, and the reaction system is stirred and reacted at 50° C. for 20 hours.

[0069] After the reaction was completed, filter, and the filtrate was evaporated with a rotary evaporator to remove the solvent, and the residue was purified by 300-400 mesh silica gel column chromatography to obtain the target product with a yield of 97.6% and a purity of 98.2% (HPLC).

[0070] NMR: 1 H NMR (500MHz, CDCl 3 )δ2.41(s,3H),5.76(s,2H),6.70-6.75(m,2H),6.98-7.03(m,2H),7.07-7.11(m,1H),7.31-7.37(m, 2H), 8.09-8.11 (m, 1H).

Embodiment 3

[0071] Embodiment 3: the synthesis of p-methoxyphenyl anthranilic acid

[0072]

[0073] In a dry and clean reactor, add 50ml of solvent HMPA, then add the above formula (II) compound, formula (III) compound, formula (a) copper compound and 1,10-phenanthroline in turn, so that the molar ratio is 1 :2:0.15:0.3, wherein the compound of formula (II) is 10mmol, and the reaction system is stirred and reacted at 60°C for 25 hours.

[0074] After the reaction was finished, filter, and the filtrate was rotary evaporated with a rotary evaporator to remove the solvent, and the residue was purified by 400-500 mesh silica gel column chromatography to obtain the target product as a solid, with a yield of 76.7% and a purity of 97.9% ( HPLC).

[0075] Melting point: 102-103°C;

[0076] NMR: 1 H NMR (500MHz, CDCl 3 )δ3.85(s,3H),5.78(s,2H),6.72(d,J=7.8Hz,2H),6.94(d,J=7.2Hz,2H),7.08-7.12(m,2H), 7.30-7.36 (m, 1H), 8.09-8.11 (m, 1H).

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Abstract

The invention relates to a method for compounding an amino-substituted arylate compound. The method comprises the step that under the condition of the adoption of a copper source compound catalyst and a ligand, and isatoic anhydride derivative and organic cyclic borate compound react in an organic solvent, so that the decarboxylation coupling reaction of isatoic anhydride compounds is realized, high-yield and high-purity amino-substituted arylate compound is obtained, a new compounding way is provided for the compounding of amino-substituted arylate compounds, and the method has good application prospects and industrial value.

Description

technical field [0001] The invention relates to a synthesis method of an aryl ester compound, in particular to a synthesis method of an amino-substituted aryl ester compound, and belongs to the field of organic chemical synthesis. Background technique [0002] Amino substituted aryl ester compounds are an important class of building blocks and / or intermediates in the synthesis of natural products and pharmaceutically active compounds. At the same time, this type of compound itself also has good biological activity and pharmacological activity. It is precisely because of its application potential in the field of medicine that it has attracted widespread attention from scientists, and a lot of research has been done on it, and many results have been achieved. [0003] Outside the field of medicine, in recent years, it has been found that this type of compound can also be used in the field of photochemistry, for example, it can be used as an initiator of a fluorescent marker fr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/22C07C229/56
Inventor 陈久喜吴华悦刘妙昌王庆宗高文霞黄小波
Owner JIAXING NIYA OPTOELECTRONICS CO LTD
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