Preparation method of 4-site alkylated derivative of 2-methylquinoline compound

A technology of methyl quinoline and compound is applied in the field of preparation of 4-position alkylated derivatives, which can solve the problem of large amount of carboxylic acid, and achieve the advantages of less side reaction products, good substrate solubility and wide applicability. Effect

Active Publication Date: 2022-04-22
UNIV OF JINAN +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method can obtain alkylated products, but the amount of carboxylic acid required is relatively large (Org. Lett. 2018, 20, 6863-6867)

Method used

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  • Preparation method of 4-site alkylated derivative of 2-methylquinoline compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] -Methylquinoline (1 mmol), acetic acid (2.0 mmol), silver nitrate (0.5 mmol), Selectfluor (4 mmol) and magnetons were added to the aqueous solution (10 ml) and reacted at 80 ℃ for 8 h, and 20 ml Add water and 20 ml ethyl acetate, stir rapidly with sodium bicarbonate until no bubbles are generated, extract with ethyl acetate (3*20 mL), combine the organic layers, dry over anhydrous sodium sulfate, filter, and concentrate. Column chromatography (eluent: ethyl acetate / n-hexane = 1:15) yielded 142.8 mg of the product 2,4-dimethylquinoline with a yield of 91%.

[0030] 1 H NMR (400 MHz, CDCl 3 ) δ 8.01 (d, J = 8.4 Hz, 1H), 7.92 (d, J = 8.3Hz, 1H), 7.69–7.62 (m, 1H), 7.48 (t, J = 7.6 Hz, 1H), 7.11 (s, 1H), 2.68 (s,3H), 2.64 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 158.56 , 147.56 , 144.20 , 129.07, 129.01 , 126.49 , 125.37 , 123.51 , 122.64 , 25.10 , 18.50 .

Embodiment 2

[0032] 2-Methylquinoline (1 mmol), propionic acid (2.0 mmol), silver nitrate (0.5 mmol), Selectfluor (4 mmol) and magnetons were added to aqueous solution (10 ml) and reacted at 80 °C for 8 h, adding Add 20 ml of water and 20 ml of ethyl acetate, add sodium bicarbonate and stir quickly until no bubbles are generated, extract with ethyl acetate (3*20 mL), combine the organic layers, dry over anhydrous sodium sulfate, filter, and concentrate. Column chromatography (eluent: ethyl acetate / n-hexane = 1:15) yielded 153.5 mg of the product 4-ethyl-2-methylquinoline with a yield of 90%.

[0033] 1 H NMR (400 MHz, CDCl 3 ) δ 8.02 (d, J = 8.3 Hz, 1H), 7.95 (d, J = 8.3Hz, 1H), 7.65–7.60 (m, 1H), 7.48–7.43 (m, 1H), 7.10 (s, 1H), 3.03 (q, J = 7.5Hz, 2H), 2.69 (s, 3H), 1.35 (t, J = 7.5 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ158.66 , 149.72 , 147.77 , 129.18 , 128.85 , 125.60 , 125.28 , 123.08 ,120.51 , 25.20 , 24.82 , 13.92 .

Embodiment 3

[0035] 2-Methylquinoline (1 mmol), isobutyric acid (2.0 mmol), silver nitrate (0.5 mmol), Selectfluor (4 mmol) and magnetons were added to aqueous solution (10 ml) and reacted at 80 °C for 8 h, adding Add 20 ml of water and 20 ml of ethyl acetate, add sodium bicarbonate and stir quickly until no bubbles are generated, extract with ethyl acetate (3*20 mL), combine the organic layers, dry over anhydrous sodium sulfate, filter, and concentrate. Column chromatography (eluent: ethyl acetate / n-hexane = 1:15) yielded 162.9 mg of the product 4-isopropyl-2-methylquinoline with a yield of 88%.

[0036] 1 H NMR (600 MHz, CDCl 3 ) δ 8.02 (t, J = 8.8 Hz, 2H), 7.63 (t, J = 7.6Hz, 1H), 7.47 (t, J = 7.6 Hz, 1H), 7.17 (s, 1H), 3.67 (dd, J = 13.7, 6.9 Hz,1H), 2.71 (s, 3H), 1.37 (s, 3H), 1.36 (s, 3H). 13 C NMR (150 MHz, CDCl 3 ) δ158.71 , 154.16 , 147.98 , 129.38 , 128.69 , 125.22 , 125.04 , 122.79 ,117.63 , 28.09 , 25.41 , 22.80 .

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of a No.4 alkylated derivative of a 2-methylquinoline compound, which is realized by the following steps: mixing the 2-methylquinoline compound and carboxylic acid, and reacting under the catalysis of silver nitrate by taking Selectfluor as an oxidizing agent to obtain the No.4 alkylated derivative of the 2-methylquinoline compound. And carrying out column chromatography to obtain the No.4 alkylated derivative of the 2-methylquinoline compound. According to the method provided by the invention, Selectfluor is used as an oxidizing agent, the method is carried out in an aqueous solution under the catalysis of silver nitrate, the solubility of a substrate is good, and the applicability is wide; and the reaction yield is high, and the controllability is strong. The method provided by the invention is green and environment-friendly, few in side reaction products, green and efficient.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of a No. 4 alkylated derivative of a 2-methylquinoline compound. Background technique [0002] The 4th-alkylated derivatives of 2-methylquinoline compounds belong to quinoline compounds. In natural products and medicines, quinoline and its derivatives are ubiquitous and have a wide range of biological activities. Quinoline and its derivatives are very important nitrogen-containing heterocyclic compounds, which can be widely used in the fields of drugs, fungicides, herbicides, corrosion inhibitors and functional materials. According to reports, quinoline and its derivatives have a wide range of biological activities such as anticancer, antibacterial, anti-inflammatory, and anti-HIV. In addition, quinoline heterocycles are often introduced into drug molecules as the parent structure of medicines or pesticides. Therefore, the synthesis of...

Claims

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Application Information

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IPC IPC(8): C07D215/04C07D215/18C07D215/12
CPCC07D215/04C07D215/18C07D215/12
Inventor 王守锋宋莹悦王文贵冯威李金峰
Owner UNIV OF JINAN
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