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Synthesis method of 2-ethoxybenzoic acid compound

A technology of ethoxybenzoic acid and synthesis method, which is applied in organic chemistry, amide preparation, etc., can solve the problems of harsh reaction conditions and difficult separation of product-directing groups, and achieve simple reaction system, good substrate universality, The effect of low catalyst cost

Active Publication Date: 2015-02-25
ZHENGZHOU UNIV
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Problems solved by technology

[0003] The technical problem to be solved by the present invention is to provide a kind of 2-ethoxybenzoic acid for the direct functionalization of C-H bond to synthesize 2-ethoxybenzoic acid with harsh reaction conditions and problems such as the product directing group is difficult to detach from after the reaction. The synthetic method of formic acid compound, this method uses cheap metal as catalyst and is simple and efficient

Method used

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The steps of the synthetic method of the 2-ethoxybenzoic acid of the present embodiment are as follows:

[0021] (1) Preparation of 2-ethoxybenzamidopyridine-1-oxide: Benzamidopyridine-1-oxide (0.2 mmol, 42.8 mg), anhydrous CuCl (0.2 mmol, 19.6 mg) , put it into a high-pressure sealed tube, then inject 0.75 mL of ethanol and 0.75 mL of pyridine, stir at room temperature for 30 minutes, and add K after the complex precipitates. 2 CO 3 (0.1 mmol, 13.8 mg), the reaction system was heated to 130 °C and reacted for 12 h. After the reaction was completed, dilute hydrochloric acid (5 mL, 2N) was added to quench the reaction, and then the reaction solution was washed with CH 2 Cl 2 (10×3 mL) extraction, drying over anhydrous sodium sulfate, separation by thin layer chromatography (CH 2 Cl 2 / acetone) to obtain 43 mg of 2-ethoxyamides, yield 84%, melting point 140-141 °C. 1 H NMR (400 MHz, CDCl 3 ) δ 12.30 (s, 1H), 8.73 (d, J = 8.4 Hz, 1H), 8.31-8.28 (m, 2H), 7.55-7.51 ...

Embodiment 2

[0024] The synthetic method of the 4-methylbenzoic acid of the present embodiment is as follows:

[0025] (1) Preparation of 2-(4-methyl-2-ethoxybenzamido)pyridine-1-oxide: According to the method described in Example 1, the difference is that the substrates and reagents used are: 2 -(4-Methyl-benzamido)pyridine-1-oxide (0.2 mmol, 45.6 mg), CuCl (0.2 mmol, 19.6 mg), K 2 CO 3 (0.1 mmol, 13.8 mg), EtOH 0.75 mL, pyridine 0.75 mL, and reacted at 130 °C for 12 h to obtain 2-(4-methyl-2-ethoxybenzamido)pyridine-1-oxide 46 mg, solid, 85% yield. Melting point 162-163 ℃. 1 H NMR (400 MHz, CDCl 3) δ 12.16 (s, 1H), 8.66 (d, J = 8.4 Hz, 1H), 8.20-8.18 (m, 1H), 8.09-8.07 (d, J = 8.0 Hz, 1H), 7.26-7.23 (m, 1H), 6.91-6.88 (m, 1H), 6.83 (d, J = 8.0 Hz, 1H), 6.77 (s, 1H), 4.24 (q, J = 7.0 Hz, 2H), 2.32 (s, 3H), 1.63 (t, J = 7.0 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 164.0, 157.4, 145.5, 137.4, 132.5, 127.9, 122.0, 118.3, 117.8, 115.7, 113.0, 65.2, 21.9, 14.8. HRMS (ESI) Calcd....

Embodiment 3

[0028] The preparation method of the 4-tert-butylbenzoic acid of the present embodiment is as follows:

[0029] (1) Preparation of 2-(4-tert-butyl-2-ethoxybenzamido)pyridine-1-oxide: according to the method described in step (1) of Example 1, the difference is the substrate used and the reagents were: 2-(4-tert-butyl-benzamido)pyridine-1-oxide (0.2 mmol, 54.0 mg), CuCl (0.2 mmol, 19.6 mg), K 2 CO 3 (0.1 mmol, 13.8 mg), EtOH 0.75 mL, pyridine 0.75 mL, react at 130 °C for 12 h. To obtain 2-(4-tert-butyl-2-ethoxybenzamido)pyridine-1-oxide 52 mg, solid, 83% yield. Melting point 127-128 ℃. 1 H NMR (400 MHz, CDCl 3 ) δ 12.27 (s, 1H), 8.75 (dd, J = 8.5 Hz, J = 1.7 Hz, 1H), 8.29 (dd, J = 6.5 Hz, J = 1.0 Hz, 1H), 8.20 (d, J = 8.3 Hz, 1H), 7.37-7.33 (m, 1H), 7.14 (dd, J = 8.4 Hz, J = 1.7 Hz, 1H), 7.05 (d, J = 1.6 Hz, 1H), 7.00-6.96(m, 1H), 4.37 (q, J = 7.0 Hz, 2H), 1.73 (t, J = 7.0 Hz, 3H). 1.36 (s, 9H). 13 C NMR (100 MHz, CDCl 3 ) δ 164.0, 158.6, 157.3, 145.5...

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Abstract

The invention discloses a synthesis method of a 2-ethoxybenzoic acid compound. The synthesis method comprises the following steps of orderly adding aromatic acylaminopyridine-1-oxide, cuprous chloride and an organic solvent into a reactor, stirring the mixture at a room temperature for 25-35min, adding potassium carbonate into the mixture after complex precipitates are produced, heating the reaction system to a temperature of 125-135 DEG C to cause a reaction lasting for 10-15h, after the reaction, carrying out extraction, drying, condensation and chromatographic separation to obtain an ethoxylated product, and carrying out alkaline hydrolysis and acidification to obtain the 2-ethoxybenzoic acid compound. The synthesis method has the advantages of easy acquisition of raw materials, cheap catalyst, mild reaction system, operation simpleness, high yield and substrate universality. The synthesis method has the yield of 87% and can realize guide base removal under mild conditions.

Description

technical field [0001] This paper relates to a kind of synthetic method of 2-ethoxybenzoic acid compound. The method is to introduce benzoic acid as a starting material N - O The bidentate directing group can efficiently obtain 2-ethoxy compounds under the catalysis of cuprous chloride, and finally remove the directing group to obtain 2-ethoxybenzoic acid compounds. Background technique [0002] 2-Ethoxybenzoic acid compounds are an important class of medical materials, which have analgesic and anti-inflammatory effects in medical experiments, and are widely used in the synthesis of antagonists of sildenafil and arginine antidiuretic hormone receptors V1A and V2 Among them, the efficient synthesis of 2-ethoxybenzoic acid compounds has attracted widespread attention. Since the direct functionalization of the C-H bond does not require pre-functionalization of the raw materials, the synthesis steps are short, environmentally friendly, and has many advantages such as high ato...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/21C07C65/24C07C51/06
CPCC07C51/06C07D213/89C07C65/21C07C65/24
Inventor 牛俊龙张林宝张守坤郝新奇任保增宋毛平
Owner ZHENGZHOU UNIV
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