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Synthesis method of amide aryl compound

A kind of aryl amide, synthesis method technology, applied in the direction of preparation of organic compound, formation/introduction of amide group, chemical instrument and method etc.

Inactive Publication Date: 2017-03-15
中国人民解放军63975部队
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In addition, transition metal-catalyzed preparation of aryl amides using aryl halides as reaction substrates has also been reported frequently.

Method used

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  • Synthesis method of amide aryl compound
  • Synthesis method of amide aryl compound
  • Synthesis method of amide aryl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of benzamide (3a) from benzoic acid (1a) and DMF (2a):

[0027]

[0028] Add benzoic acid (0.036g, 0.3mmol), Xantphos (0.017g, 0.03mmol), K 2 S 2 o 8 (0.162g, 0.6mmol), Ru(p-cymene)Cl 2 (0.0092g, 0.015mmol), DMF (2mL), fill it with argon gas, tighten the bottle cap, and seal the reaction at an external temperature of 160°C for 12h; monitor the complete reaction by gas chromatography; filter the reaction solution, remove the solvent by rotary evaporation, and pass through the column After separation by chromatography (ethyl acetate:n-hexane=1:1), a colorless transparent liquid 3a was obtained with a yield of 88%.

[0029] 1 H NMR (300MHz, CDCl 3 )δ7.39(s, 5H), 3.10(s, 3H), 2.96(s, 3H); 13 C NMR (75MHz, CDCl 3 )δ171.76(s), 136.34(s), 129.61(s), 128.43(s), 127.11(s), 39.69(s), 35.43(s); MS(70eV, EI) m / z(EI) C 9 h 11 NO[M]: 149.19, 51(36), 77(100), 105(29), 148(56), 149(5).

Embodiment 2

[0031] Synthesis of 3-methylbenzamide (3b) from 3-methylbenzoic acid (1b) and DMF (2a):

[0032]

[0033] Add 3-methylbenzoic acid (0.041g, 0.3mmol), Xantphos (0.017g, 0.03mmol), K 2 S 2 o 8 (0.162g, 0.6mmol), Ru(p-cymene)Cl 2 (0.0092g, 0.015mmol), DMF (2mL), fill it with argon gas, tighten the bottle cap, and seal the reaction at an external temperature of 160°C for 12h; monitor the complete reaction by gas chromatography; filter the reaction solution, remove the solvent by rotary evaporation, and pass through the column After separation by chromatography (ethyl acetate:n-hexane=1:1), a colorless transparent liquid 3b was obtained with a yield of 90%.

[0034] 1 H NMR (300MHz, CDCl 3 )δ7.23(dq, J=13.0, 7.4Hz, 4H), 3.04(d, J=39.5Hz, 6H), 2.37(s, 3H); 13 C NMR (75MHz, CDCl3 )δ171.94(s), 138.28(s), 136.37(s), 130.28(s), 128.24(s), 127.73(s), 124.05(s), 39.68(s), 35.38(s), 21.45( s); MS (70eV, EI) m / z (EI) C 10 h 13 NO[M]: 163.22, 65(27), 91(100), 119(33), 162(28), 16...

Embodiment 3

[0036] Synthesis of 4-hydroxybenzamide (3c) from 4-hydroxybenzoic acid (1c) and DMF (2a):

[0037]

[0038] Add 4-hydroxybenzoic acid (0.041g, 0.3mmol), Xantphos (0.017g, 0.03mmol), K 2 S 2 o 8 (0.162g, 0.6mmol), Ru(p-cymene)Cl 2 (0.0092g, 0.015mmol), DMF (2mL), fill it with argon gas, tighten the bottle cap, and seal the reaction at an external temperature of 160°C for 12h; gas chromatography monitors that the reaction is complete; filter the reaction solution, remove the solvent by rotary evaporation, and pass through the column After separation by chromatography (ethyl acetate:n-hexane=1:1), a white solid 3c was obtained with a yield of 83%.

[0039] 1 H NMR (300MHz, CDCl 3 )δ7.25-7.19 (m, 2H), 6.74-6.66 (m, 2H), 3.06 (d, J=19.0Hz, 6H); 13 C NMR (75MHz, CDCl 3 )δ172.82(s), 158.77(s), 129.20(s), 126.31(s), 115.50(s), 38.04(d, J=321.6Hz); MS(70eV, EI) m / z(EI) C 9 h 11 NO 2 [M]: 165.19, 63(26), 65(100), 73(44), 93(83), 121(82), 164(28), 165(3).

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Abstract

The invention relates to a synthesis method of an amide aryl compounds. According to the method, Ru-(p-cymene) C12 is taken as a catalyst, K2S2O8 is taken as an oxidizing agent, Xantphos is taken as a ligand, one reactant (N, N-dialkyl formamide) is taken as a solvent, and a substrate aryl carboxylic acid and the N, N-dialkyl formamide are subjected to coupling reaction, so that the amide aryl compound is obtained. The reaction substrate is low in cost and easy to get, stable in performance, small in toxicity and mild in reaction conditions, and has a wide applicability for substrate with different functional groups. The amide aryl compound efficiently established through the synthesis method belongs to an important molecular skeleton of various medicines, bioactive molecules and natural products, and the synthesis method provides a widely applicable preparation method for the synthesis of the compounds.

Description

technical field [0001] The invention relates to a method for synthesizing arylamide compounds. Background technique [0002] In organic synthesis, the amide bond is a very important functional group, and the shadow of the amide bond can be seen in many organic compounds, biologically active compounds and natural products. Since Heck reported the amidation reaction catalyzed by Pd in ​​1974 ((a) A.Schoenberg, I.Bartoletti and R.F.Heck, J.Org.Chem., 1974,39,3318-3326; (b) A.Schoenberg and R.F.Heck, J.Org.Chem., 1974, 39, 3327-3331), methods for preparing amide compounds emerge in endlessly, including reports on different substrates, different catalysts, and different methods. [0003] The most classic reaction for the preparation of aryl amides is to use aryl carboxylic acid as a substrate, add an activating reagent, and then react with a dialkylamine to generate the corresponding aryl formamide. This type of reaction usually requires the addition of an excess of activating r...

Claims

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Application Information

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IPC IPC(8): C07C231/10C07C233/65C07C235/46C07C237/30C07C253/30C07C255/57C07D213/81C07D295/192C07B43/06
CPCC07B43/06C07C231/10C07C253/30C07D213/81C07D295/192C07C233/65C07C235/46C07C237/30C07C255/57
Inventor 肖军华毕晓静李君臣王红梅
Owner 中国人民解放军63975部队
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