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Preparation method of quinoline compound

A technology of compounds and quinolines, which is applied in the field of preparation of quinolines, can solve problems such as cumbersome operation steps and difficult access to substrates

Inactive Publication Date: 2016-02-03
HARBIN INST OF TECH AT WEIHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, many research works still have some deficiencies, such as difficult access to substrates, cumbersome operation steps, and the need for additional oxidizing agents (J.Org.Chem.2012, 32, 815-824) or reducing agents (ChemCatChem2015,7,349-353) and other shortcomings

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  • Preparation method of quinoline compound
  • Preparation method of quinoline compound

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Embodiment Construction

[0010] The reaction process is like figure 2 Show:

[0011] figure 2 Reactor: R 1 R 2 R 3 R 4 R 7 It is hydrogen atom, alkyl, aromatology, halogen, alky oxygen, aroma oxygen, trifluoro methyl, etc., R 5 R 6 It is hydrogen atom, alkyl, aromatics.

[0012] Example of specific preparation methods: 0.1 millroretol, 0.1 mlmorezide, 0.2 mmol uncle butanol potassium (alkali) and 1 ml of methanol, mix at 55 ~ 65 ° C temperatureThe reaction is 24 hours.After the reaction is over, organic solvent washing, concentration, and column layer is pure, which obtains 2-phenyl phenoline, and the income is 76%.The melting point is 82 ~ 84 ° C; MRI hydrogen spectrum 1 HNMR (400MHz, CDCL 3 ) Δ8.23 (d, J = 8.5Hz, 2H), Δ8.18 (D, J = 7.4Hz2H), 7.88 (D, J = 8.6Hz, 1H), 7.83 (D, J = 8.1Hz, 1H), 7.74 (T, J = 7.8Hz, 1H), 7.56–7.46 (m, 4H); MRI 13 CNMR (100MHz, CDCL 3 1285,1256,1177,1028,831,813,773; High -resolution mass spectrometry HRMS (ESI) M / Z: CalcdForc15H11NNA [M+Na]+: 228.0784.found: 228.0761.

[001...

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Abstract

The invention relates to a preparation method of a quinoline compound. The structural formula of the prepared quinoline compound is shown as the figure attached in the specification, wherein R1, R2, R3, R4 and R7 are hydrogen atom, alkyl, aryl, halogen, alkoxy, aryloxy, trifluoromethyl and the like, R5 and R6 are hydrogen atom, alkyl and aryl. The preparation method includes: taking 2-nitrobenzyl alcohol and acetophenone as raw materials, under alkaline catalysis, carrying out complete stirring reaction at 55-65DEG C for 24h, at the end of the reaction, extraction, performing extraction, organic solvent washing, concentration, and column chromatography purification to obtain a quinoline compound with a yield of 60-85%. Specifically, the alkaline is potassium tert-butoxide, potassium hydroxide and sodium hydroxide, etc. The method provided by the invention has the characteristics of stable and easily available raw materials, mild reaction conditions, good product selectivity, simple operation, and suitability for industrial production, etc.

Description

Technical field [0001] The present invention involves a preparation method for a pyrodoline -type compound. Background technique [0002] Pacinoline and its derivatives are important skeleton for many organic compounds, and have many applications ( Chem.rev., 2005,105,559 To.The unit of pyrine is continuously used to design a simple structure or related structure of many modern drugs, such as antibacterial agents ( Bioorg.Med.chem, 2007,15,1280; Eur.j.Med.chm., 2015,97: 335–355 ), Anti -cancer drug ( EUR.J.Med.chem., 2015,92: 91–102 ), Antifungal agent ( Org.lett., 2012,14 (4): 1012–1015 ), Anti -malaria agent ( Bioorg.med.chm.2003,11,1531 ) And anti -psychiatric drugs ( Nature, 1998,392,289 To.In recent years, many domestic and foreign research groups have made certain modifications and improvements on FRIEDL? NDER pyrine synthesis method. Traditional Friedl? NDER pyrodine synthesis method has become a hotspot for pyrine synthesis.However, many research work still has some short...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/06
CPCC07D215/06
Inventor 王琦吴彦超李惠静吉元昭南祥
Owner HARBIN INST OF TECH AT WEIHAI