Preparation method of methyl 4-(dimethoxymethyl)quinoline-2-carboxylate derivative

A technology of dimethoxymethyl and methyl formate, applied in the direction of organic chemistry, can solve problems such as complex preparation methods, and achieve the effects of high reaction yield, strong controllability, and good solubility

Active Publication Date: 2019-08-23
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the common preparation method of acetal needs to be catalyzed by anhydrous acid, and the preparation method is relatively complicated.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Quinoline-2-carboxylic acid methyl ester (1mmol, 187mg), Selectfluor (4mmol, 1.4g) and AgNO 3 (2mmol, 340mg) was added to methanol solution (50ml,) and reacted at 80°C for 24h, neutralized with saturated sodium bicarbonate solution, extracted with ethyl acetate (3*10mL), combined organic layers, washed with saturated brine (20mL), Dry over anhydrous sodium sulfate, filter and concentrate. Column chromatography (eluent: ethyl acetate / n-hexane = 1:3) yielded 261 mg of the product 4-(dimethoxymethyl)quinoline-2-carboxylic acid methyl ester, with a yield of 72%.

[0023] 1 H NMR (600 MHz, CDCl 3 ) δ 8.41 (s, 1H), 8.33 (d, J = 2.0 Hz, 1H), 8.27(d, J = 9.0 Hz, 1H), 7.73 (dd, J = 9.0, 2.1 Hz, 1H), 5.88 (s, 1H), 4.09 (s,3H), 3.38 (s, 6H).

Embodiment 2

[0025] Methyl 6-fluoroquinoline-2-carboxylate (1mmol, 205mg), Selectfluor (4mmol, 1.4g) and AgNO 3 (2mmol, 340mg) was added to methanol solution (50ml) and reacted at 80°C for 24h, neutralized with saturated sodium bicarbonate solution, extracted with ethyl acetate (3*10mL), combined organic layers, washed with saturated brine (20mL), Dry over sodium sulfate, filter, and concentrate. Column chromatography (eluent: ethyl acetate / n-hexane = 1:3) yielded 192 mg of the product 6-fluoro-4-(dimethoxymethyl)quinoline-2-carboxylic acid methyl ester, with a yield of 69% .

[0026] 1 H NMR (600 MHz, CDCl 3 ) δ 8.41 (s, 1H), 8.35 (dd, J = 9.3, 5.6 Hz,1H), 7.97 (dd, J = 10.1, 2.6 Hz, 1H), 7.57 (td, J = 9.4, 2.7 Hz, 1H), 5.85(s, 2H), 4.09 (s, 4H), 3.38 (s, 7H).; 13 C NMR (151 MHz, CDCl 3 ) δ 165.73, 161.79(d, J = 252.0 Hz), 146.99 (d, J = 3.0 Hz), 145.21, 143.62 (d, J = 6.1 Hz), 133.85 (d, J = 9.6 Hz), 127.92 (d, J = 10.7 Hz), 120.64 (d, J = 26.2 Hz), 120.13, 108.30...

Embodiment 3

[0028] 7-Chloroquinoline-2-carboxylic acid methyl ester (1mmol, 221mg), Selectfluor (4mmol, 1.4g) and AgNO 3 (2mmol, 340mg) was added to methanol solution (50ml) and reacted at 80°C for 24h, neutralized with saturated sodium bicarbonate solution, extracted with ethyl acetate (3*10mL), combined organic layers, washed with saturated brine (20mL), Dry over sodium sulfate, filter, and concentrate. Column chromatography (eluent: ethyl acetate / n-hexane = 1:3) yielded 212 mg of the product 7-chloro-4-(dimethoxymethyl)quinoline-2-carboxylic acid methyl ester, with a yield of 69% .

[0029] 1 H NMR (600 MHz, CDCl 3 ) δ 8.38 (s, 1H), 8.34 (d, J = 1.7 Hz, 1H), 8.29(d, J = 9.0 Hz, 1H), 7.62 (dd, J = 9.0, 1.8 Hz, 1H), 5.90 (s, 1H), 4.09 (s,3H), 3.37 (s, 6H).; 13 C NMR (151 MHz, CDCl 3 ) δ 165.61, 148.58, 148.54, 144.33, 136.14, 129.94, 129.80, 125.77, 125.21, 119.64, 100.30, 53.34, 53.07.

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of a methyl 4-(dimethoxymethyl)quinoline-2-carboxylate derivative. The method is realized by the following steps that under catalysis of Selectfluor/AgNO3, methyl quinoline-2-carboxylateor a derivative thereof reacts with methanol, and a methyl 4-(dimethoxymethyl)quinoline-2-carboxylate derivative is obtained after column chromatography. The method provided by the invention is carried out in methanol solution under the catalysis of Selectfluor/AgNO3, and has the advantages of good substrate solubility, wide applicability, high reaction yield and high controllability. The preparation method provided by the invention is environment-friendly, has few side reaction products, andhas high efficiency.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of methyl 4-(dimethoxymethyl)quinoline-2-carboxylate derivatives. Background technique [0002] Quinoline compounds have a wide range of pharmaceutical activities, such as anti-HIV, anti-inflammatory and anti-tumor. Acetal is a condensation product of one molecule of aldehyde and two molecules of alcohol. Acetal is stable to alkali, and this property is often used to protect carbonyl in organic synthesis. However, the common preparation method of acetal needs to be catalyzed by anhydrous acid, and the preparation method is relatively complicated. Therefore, developing a new method for preparing acetal has become a technical problem to be solved urgently. Contents of the invention [0003] Aiming at the problems existing in the prior art, the invention provides a kind of preparation method of 4-(dimethoxymethyl) quinoline-2-formic ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/48
CPCC07D215/48
Inventor 张莹莹于泽慧董广露王守锋
Owner UNIV OF JINAN
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