Preparation method of N-phenyl-N-[8]quinolyl-4-fluoro-benzamide

Abstract

The invention relates to a preparation method of N-phenyl-N-[8]quinolyl-4-fluoro-benzamide. The preparation method comprises the following steps: adding 4-fluoro-benzoyl 8-aminoquinoline, anhydrous copper acetate, triphenyl bismuth, sodium bicarbonate, a 1,4-dioxane solvent and one No.5 magneton into a reactor in sequence; after introducing condensed water into a condensing tube from bottom to top, putting the reactor into an oil-bath pot and carrying out heating reaction; after finishing the reaction, pouring a reaction solution into a separating funnel; adding distilled water and extracting with ethyl acetate for 3 times; combining obtained organic phases and carrying out spin-drying through a rotary evaporator; separating and purifying a crude product through a column chromatography to obtain the N-phenyl-N-[8]quinolyl-4-fluoro-benzamide, wherein the yield is 93 percent. The preparation method provided by the invention has moderate conditions; a cheap metal copper catalyst is adopted, nitrogen gas protection is not adopted, and an oxidant is not needed, so that the preparation method has relatively good economic efficiency and is environmentally friendly; the product can be applied to various fields including drug synthesis, pesticide synthesis, synthesis of corrosion inhibitors of buildings and the like.

Description

technical field [0001] The invention relates to a preparation method for transition metal catalyzed synthesis of aromatic amide compounds, in particular to a preparation method for N-phenyl-N-[8]quinolyl-4-fluoro-benzamide. Background technique [0002] Amide compounds are not only the components of proteins, but also play the role of nitrogen storage and nitrogen supply in life activities, and are important elements in the formation of amide bonds in proteins, polypeptides and biological enzymes. In addition, amides are also used in the production of polyamide polymer materials - nylon. And aryl-containing amide compounds are mostly used in the production of pharmaceuticals in the pharmaceutical industry, especially quinoline amides, which have been found to have obvious anti-malarial effects since they were discovered in the 1930s; clinical studies have also shown that quinoline amides contain Many drugs of morphine also have various biological activities such as anti-tum...

AI Technical Summary

Problems solved by technology

After 1970, cross-coupling reactions catalyzed by Pd and Ni gradually appeared. Although the reaction conditions under these catalysts are mild and simple, the catalysts are highly toxic, expensive and highly dependent on unstable and highly toxic organophosphorus ligands. is the Achilles' heel of this type of catalytic reaction

[0004] In 1996, on the premise of Barton's early research results on amide arylation, Dominic M.T.Chan used triaryl bismuth and copper acetate as catalysts for the first time, and invented a kind of acetanilide compounds at room temperature with pyridine as a ligand. The arylation reaction of various N-H-containing compounds such as heterocyclic compounds, but the arylation reaction of the N-H bond of 8-aminoquinoline compounds has not been realized

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