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Synthesis method of phenyl(quinolin-8-yl)-one derivative

A synthesis method and technology of derivatives, applied in the direction of organic chemistry, etc., can solve the problems of difficult availability, high price of metal catalysts and raw materials, and achieve the effects of simple operation and high yield.

Active Publication Date: 2021-08-06
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the main method is to synthesize 8-benzoyl with 8-formyl quinoline such as 8-quinoline formaldehyde, 8-quinoline formate, 8-acetyl quinoline, etc. under the catalysis of metal Rh or Ru. Quinoline and its derivatives, but the metal catalysts and raw materials used in these methods are relatively expensive and not easy to obtain

Method used

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  • Synthesis method of phenyl(quinolin-8-yl)-one derivative
  • Synthesis method of phenyl(quinolin-8-yl)-one derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] 4-(quinoline-8-formyl)methyl benzoate preparation: add 8-methylquinoline (0.1mmol), 4-iodobenzoic acid methyl ester (0.15 mmol), 0.01 mmol of palladium acetate, 0.15 mmol of silver carbonate, 0.12 mmol of potassium acetate, then add 1 mL of a mixed solution of hexafluoroisopropanol and glacial acetic acid (V / V=3:7), seal the tube, Heat the reaction at 130°C for 24 hours, add the reaction mixture to 30 mL of ethyl acetate to dilute, then wash with saturated sodium carbonate solution, dry the separated organic layer with anhydrous magnesium sulfate, filter to remove magnesium sulfate, and obtain the crude product The organic solution was evaporated under reduced pressure to remove the solvent, and the residue was purified by column chromatography to obtain the target product (eluent V / V: petroleum ether: ethyl acetate = 8:1).

Embodiment 2

[0012] Preparation of 4-(5-bromoquinoline-8-formyl)methyl benzoate: Add 5-bromo-8-methylquinoline (0.1mmol) and 4-iodo Methyl benzoate (0.15mmol), the palladium acetate of 0.01 mmol, the silver carbonate of 0.15 mmol, the potassium acetate of 0.12 mmol, then add the mixed solution of 1mL hexafluoroisopropanol and glacial acetic acid (V / V=3: 7), seal the tube, heat and react at 130°C for 24 hours, add the reaction mixture to 30mL ethyl acetate to dilute, then wash with saturated sodium carbonate solution, dry the separated organic layer with anhydrous magnesium sulfate, filter to remove sulfuric acid Magnesium, to obtain the organic solution of the crude product, the solvent was removed by rotary evaporation under reduced pressure, and the residue was purified by column chromatography to obtain the target product (eluent V / V: petroleum ether: ethyl acetate=8:1).

Embodiment 3-10

[0014] Embodiment 3-0 is similar to Embodiment 1 and 2. The reaction raw materials, reaction conditions and yields of each embodiment are shown in Table 1 below.

[0015] The reaction raw material of table 1 embodiment 1-10, reaction condition and productive rate

[0016]

[0017] As can be seen from Table 1, the method of the present invention has easy-to-obtain raw materials, simple and safe operation, high yield and convenient post-treatment, thus having great implementation value and potential social and economic benefits.

[0018] The characterization data of the obtained compound are as follows.

[0019] Methyl 4-(quinoline-8-formyl)benzoate (3a)

[0020] 1 H NMR (400MHz, CDCl 3 )δ8.83(dd, J=4.4Hz, 1.6Hz, 1H), 8.26(dd, J=8.4Hz, 1.6Hz, 1H), 8.08-8.06(m, 2H), 8.01(dd, J=8.2Hz ,1.4Hz,1H),7.88-7.86(m,2H),7.80(dd,J=7.0Hz,1.4Hz,1H),7.67(dd,J=8.0Hz,7.2Hz,1H),7.45(dd, J=8.0,4.0Hz,1H),3.93(s,3H); 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ197.3, 166.3, 150.8, 145.7, 141.1, 138.4, ...

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Abstract

A synthesis method of a phenyl(quinolin-8-yl)-one derivative comprises the following steps: by taking 8-methylquinoline or substituted 8-methylquinoline and aryl iodide as raw materials, Ag2CO3 as an additive, KOAc as alkali and Pd(OAc)2 as a catalyst, reacting the raw materials in a solution formed by mixing hexafluoroisopropanol and glacial acetic acid according to a volume ratio of 3: 7, sealing a tube at 130 DEG C, and reacting for 24 hours to generate the target product. The synthesis process route is simple, and the highest yield reaches 87%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to palladium acetate (Pd(OAc) 2 ) Catalyzing the method for synthesizing 8-benzoylquinoline derivatives by catalyzing 8-methylquinoline or substituted 8-methylquinoline and aryl iodide. Background technique [0002] 8-benzoylquinoline and its derivatives are an important class of quinoline organic molecules. These compounds containing 8-benzoylquinoline structural units can not only be used for the synthesis of important functional quinoline derivatives (Wentzel, M.T.; Reddy, V.J.; Hyster, T.K.; Douglas, C.J. Chemoselectivity in Catalytic C-C and C-H Bond Activation: Controlling Intermolecular Carboacylation and Hydroarylation of Alkenes. Angew. Chem. Int. Ed.2009, 48, 6121-6123; Dreis, A.M.; C.J.Catalytic Carbon-Carbonσ-Bond Activation: An Intramolecular Carbo-Acylation Reaction with Acylquinolines.J.Am.Chem.Soc.2009,131,412 -413.), and there are many molecules of this type...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/14C07D215/18
CPCC07D215/14C07D215/18
Inventor 王文蓉李团结成立
Owner XUZHOU NORMAL UNIVERSITY
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