112811-65-1Relevant articles and documents
Synthesis method of 2, 4, 5-trifluoro-3-methoxybenzoyl chloride
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Paragraph 0053; 0063-0066; 0073; 0079-0080; 0083; 0089-0090, (2020/09/16)
The invention discloses a synthesis method of 2, 4, 5-trifluoro-3-methoxybenzoyl chloride. The method comprises the following steps of: (1) using a metal halide as a catalyst, putting N-methyltetrafluorophthalimide in an alkaline environment, and carrying out hydroxylation reaction to obtain a sodium salt of 4-hydroxy-3, 5, 6-trifluorophthalic acid; (2) adding acid into the reaction system, and carrying out decarboxylation reaction to obtain 2, 4, 5-trifluoro-3-hydroxybenzoic acid; (3) sequentially adding a methylation reagent and acid into the reaction system under an alkaline condition, andcarrying out methylation reaction and acidification reaction to obtain 2, 4, 5-trifluoro-3-methoxybenzoic acid; and (4) mixing the 2, 4, 5-trifluoro-3-methoxybenzoic acid with thionyl chloride, and carrying out acylation reaction so as to obtain the 2, 4, 5-trifluoro-3-methoxybenzoyl chloride. The synthesis method disclosed by the invention is short in route, small in alkali dosage and few in sidereaction, the total molar yield of the reaction reaches 82.5%, and the purity of the product reaches 99.6% or above.
One-pot process for preparing 2,trifluoro -3 - methoxybenzoic acid (by machine translation)
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Paragraph 0056; 0066-0071; 0072; 0078; 0079; 0080; 0086-0087, (2020/09/23)
The method comprises the following steps: obtaining -3 - hydroxyl salt 4 - and -3 trifluoroortho-phthalate; and the method comprises the following steps: taking a metal halide as a catalyst, putting N - methyltetrafluoro phthalimide into a basic environment, and obtaining the 5,6 -hydroxy salt 4 - and -3 trifluoroortho-benzoate through hydrolysis defluorination and hydroxylation reaction 5,6 . The raw material cost is low, the process route is short, 4 - hydroxyl salt -3 and 5,6 -trifluoroortho-phthalate are synthesized only by about 8 - 10 hours, the base is reduced by 50% or more, the side reaction is less or complete, 85%, and the product purity can reach above 99.8%. (by machine translation)
Synthesis and antimycobacterial evaluation of newer 1-cyclopropyl-1,4-dihydro-6-fluoro-7-(substituted secondary amino)-8-methoxy-5-(sub)-4-oxoquinoline-3-carboxylic acids
Senthilkumar, Palaniappan,Dinakaran, Murugesan,Banerjee, Debjani,Devakaram, Ruth Vandana,Yogeeswari, Perumal,China, Arnab,Nagaraja, Valakunja,Sriram, Dharmarajan
, p. 2558 - 2569 (2008/09/21)
Thirty-four newer 1-cyclopropyl-1,4-dihydro-6-fluoro-7-(substituted secondary amino)-8-methoxy-5-(sub)-4-oxoquinoline-3-carboxylic acids were synthesized from 1,2,3,4-tetrafluoro benzene and evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant M. tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase. Among the synthesized compounds, 7-(1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinolin-2(1H)-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylic acid (13n) was found to be the most active compound in vitro with MIC of 0.16 and 0.33 μM against MTB and MDR-TB, respectively. In the in vivo animal model 13n decreased the bacterial load in lung and spleen tissues with 2.54 and 2.92 - log10 protections, respectively, at the dose of 50 mg/kg body weight. Compound 13n also inhibited the supercoiling activity of mycobacterial DNA gyrase with IC50 of 30.0 μg/ml.