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A kind of preparation method of 2-phenylquinoline compound

A technology of phenylquinoline and compounds, applied in the field of preparation of 2-phenylquinoline compounds, capable of solving problems such as high reaction temperature

Active Publication Date: 2021-01-22
威海海洋生物医药产业技术研究院有限公司
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Problems solved by technology

When using o-nitrobenzaldehyde and acetophenone as raw materials, the reaction temperature is higher, and because the reaction itself is an exothermic reaction, there is a certain danger when adding a strong base (Synthesis, 2010, 2010 (10): 1678-1686. )

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  • A kind of preparation method of 2-phenylquinoline compound
  • A kind of preparation method of 2-phenylquinoline compound
  • A kind of preparation method of 2-phenylquinoline compound

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Embodiment Construction

[0011] Its reaction process is as figure 2 as shown, figure 2 In the reaction formula: where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 is a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a halogen, or a trifluoromethyl group.

[0012] Specific preparation method example 1: 0.2 mmol o-nitrotoluene, 0.2 mmol acetophenone, 0.4 mmol potassium hydroxide (alkali) and 1.0 ml dimethyl sulfoxide are mixed together, fully stirred and reacted at room temperature for 4 hours . After the reaction was completed, it was quenched with saturated ammonium chloride aqueous solution, extracted with an organic solvent, dried, filtered, concentrated, and purified by column chromatography to obtain 2-phenylquinoline with a yield of 73%. H NMR spectrum 1 H NMR (400 MHz, CDCl 3 ) δ 8.24 (d, 1H, J = 8.6 Hz), 8.17(t, 3H, J = 7.4 Hz), 7.89 (d, 1H, J = 8.6 Hz), 7.84 (d, 1H, J = 8.0 Hz), 7.74(t , 1H, J = 7.7 Hz), 7.54 (t, 3H, J = 7.3 Hz), 7.47 (m, 1H); C...

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Abstract

The invention relates to a preparation method of 2-phenylquinoline compounds. The structural formula of the prepared 2-phenylquinoline compounds is shown in the description, and R1, R2, R3, R4, R5, R6, R7, R8 and R9 in the formula are a hydrogen atom, an alkyl group, an aryl group, an alkyloxy, a halogen or a trifluoromethyl group. The preparation method comprises the following steps: stirring o-nitrotoluene compounds, acetophenone compounds, an alkali and a solvent at a temperature from room temperature to 150 DEG C for 1-24 h; and carrying out quenching after a reaction ends, and carrying out organic solvent extraction, concentration and purification to obtain the 2-phenylquinoline compounds with the yield of 47-81%. The method has the characteristics of easily available raw materials, mild reaction conditions, short reaction time and simplicity in operation.

Description

technical field [0001] The invention relates to a preparation method of 2-phenylquinoline compounds. Background technique [0002] Quinoline compounds are important pharmaceutical intermediates, which have various biological activities such as sterilization, anti-inflammation, and anti-tumor. The synthesis of quinoline compounds initially uses o-aminobenzaldehyde as the starting material, but since the raw material itself will undergo polycondensation reaction to affect the yield, the experimental method is improved by using o-aminobenzyl alcohol or o-nitrobenzaldehyde as the starting material. (European Journal of Organic Chemistry, 2008, 2008(9):1625-1631; Advanced Synthesis & Catalysis, 2015, 46(26):583-588.). When using o-nitrobenzaldehyde and acetophenone as raw materials, the reaction temperature is higher, and because the reaction itself is an exothermic reaction, there is a certain danger when adding a strong base (Synthesis, 2010, 2010 (10): 1678-1686. ). Another...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/04C07D215/18
CPCC07D215/04C07D215/18
Inventor 吴彦超赵岩岩李惠静
Owner 威海海洋生物医药产业技术研究院有限公司
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