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2-(2-Aminobenzoyl)benzoic acid derivative and preparation method thereof

An aminobenzoyl and benzoic acid technology, which is applied in the field of 2-benzoic acid derivatives and their preparation, can solve the problems of poor regioselectivity and difficult synthesis of regioselectivity, and achieves easy operation, green post-processing, and substrates. wide range of effects

Active Publication Date: 2021-12-03
XIAMEN HUAXIA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthesis of traditional 2-(2-aminobenzoyl)benzoic acid compounds is mainly obtained by the hydrolysis reaction of dibenzo[b,e]azacyclo-6,11-dione compounds, because dibenzo[b,e ] azacyclic-6, 11-diketone compound mainly obtains through the Schmidt rearrangement reaction of anthraquinone compound and sodium azide, has the shortcoming of poor regioselectivity, so 2-(2-aminobenzoyl) benzoic acid The regioselective synthesis of compounds is also more difficult

Method used

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  • 2-(2-Aminobenzoyl)benzoic acid derivative and preparation method thereof
  • 2-(2-Aminobenzoyl)benzoic acid derivative and preparation method thereof
  • 2-(2-Aminobenzoyl)benzoic acid derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of N-butyl-2-fluoro-N-(2-fluorobenzyl)benzamide

[0043]

[0044] Add 10 mmol of n-butylamine, 10 mmol of 2-fluorobenzaldehyde, 2 g of anhydrous magnesium sulfate, and 30 mL of dichloromethane into a 100 mL round bottom flask, and stir at room temperature for 2 h to obtain an imine. Filter, concentrate, add 30 mL of methanol, add 10 mmol of sodium borohydride in an ice-water bath, stir at room temperature for 1 hour, add 30 mL of water to the reaction solution, extract the mixture with dichloromethane, collect the organic phase, add anhydrous sodium sulfate to dry, and then filter , Concentrate to obtain the corresponding amine. The obtained amine was mixed with 12mmol of 2-fluorobenzoic acid, 12mmol of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI), 12mmol of 1-hydroxybenzotriazole (HOBt) 12mmol and 20mmol of diisopropylethylamine were dissolved in 20mL N,N-dimethylformamide, and stirred at room temperature for 24h. Add an appropria...

Embodiment 1-13

[0045] Following embodiment 1-13 is the preparation method of 2-(2-aminobenzoyl) benzoic acid derivative

[0046] Example 1

[0047] Preparation of 2-(2-(N-butylamino)benzoyl)benzoic acid

[0048]

[0049] Put 0.5mmol of N-butyl-2-fluoro-N-(2-fluorobenzyl)benzamide (1a), 2mmol of potassium hydroxide, and 10mL of dimethylsulfoxide in an oil bath at 100°C, and react in air 5h. Add appropriate amount of water or sodium chloride solution to stop the reaction, and cool to room temperature. The pH of the reaction solution was adjusted to acidity, diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 120.3 mg of the target product with a yield of 81%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, DMSO) δ13.03(s, 1H), 8.73(t, J=5.1Hz, 1H), 8.03–7.91(m, 1H), 7.63(dtd, J=32.4, 7.5, 1.1Hz, 2H), 7.38–7.31(m, 2H), 6.97(...

Embodiment 2

[0051] Preparation of 2-(2-(N-butylamino)benzoyl)-4-methylbenzoic acid

[0052]

[0053] Place N-butyl-2-bromo-N-(2-fluorobenzyl)-4-methylbenzamide (1b) 0.5mmol, sodium tert-butoxide 1.5mmol, N-methylpyrrolidone 2mL in 80 ℃ oil bath, the reaction 12h. Add appropriate amount of water or sodium chloride solution to stop the reaction, and cool to room temperature. The pH of the reaction solution was adjusted to acidity, diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 96.4 mg of the target product with a yield of 62%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, DMSO) δ12.84(s, 1H), 8.71(t, J=4.8Hz, 1H), 7.86(d, J=8.0Hz, 1H), 7.36(dd, J=17.5, 8.2Hz ,2H),7.13(s,1H),6.96(d,J=7.9Hz,1H),6.81(d,J=8.5Hz,1H),6.42(t,J=7.5Hz,1H),3.26(dd ,J=12.4,6.7Hz,2H),2.38(s,3H),1.73–1.55(m,2H),1.45(dq,J=14.5,7.3Hz,2H),0.96(t,J...

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Abstract

The invention discloses a preparation method of 2-(2-aminobenzoyl)benzoic acid derivative (formula 2), which comprises the compound represented by formula (1) in a solvent, in the presence of alkali, water and air to prepare The method of the present invention takes air oxygen as the oxygen source, and the raw materials used are cheap and easy to obtain, the yield is high, the atom is economical, the reaction specificity is strong, and the post-treatment is simple and green.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to 2-(2-aminobenzoyl)benzoic acid derivatives and a preparation method thereof. Background technique [0002] 2-(2-Aminobenzoyl)benzoic acid derivatives are an important class of nitrogen-containing compounds, which have biological activities of anti-hyperlipidemia and anti-oxidation. In addition, 2-(2-aminobenzoyl)benzoic acid derivatives can also be used as tridentate ligands of transition metals and ligands of di / tripeptide transporters in vivo. At the same time, 2-(2-aminobenzoyl)benzoic acid derivatives can also be used as building blocks in organic synthesis for the synthesis of various heterocyclic compounds. Therefore, the research on new synthetic methods of 2-(2-aminobenzoyl)benzoic acid compounds and their analogues has important application value and has attracted the attention of researchers in related fields. [0003] The synthesis of traditional...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/12C07C229/52C07D213/82C07D213/74
CPCC07C227/12C07D213/74C07D213/82C07C229/52
Inventor 沈金海陈婷冯亚栋游其华
Owner XIAMEN HUAXIA UNIV
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