Synthesis method of stable isotope labeled quinoxaline-2-carboxylic acid

A stable isotope and synthetic method technology, applied in the field of organic compound synthesis, can solve the problem of no synthetic preparation method found, and achieve the effect of fewer experimental steps

Inactive Publication Date: 2020-01-03
PLANTS & ANIMALS & FOOD TESTING QUARANTINE TECH CENT SHANGHAI ENTRY EXIT INSPECTION & QUARANTINE BUREAU +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

By consulting the literature and patents, no synthetic preparation method of the substance was found

Method used

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  • Synthesis method of stable isotope labeled quinoxaline-2-carboxylic acid
  • Synthesis method of stable isotope labeled quinoxaline-2-carboxylic acid
  • Synthesis method of stable isotope labeled quinoxaline-2-carboxylic acid

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preparation example Construction

[0019] A kind of synthetic method of the quinoxaline-2-carboxylic acid of stable isotope label provided by the invention comprises the following steps:

[0020] S1: After condensation reaction of 40% aqueous solution of methylglyoxal with stable isotope-labeled aniline, 2-methylquinoxaline labeled with stable isotope is reacted; The molar ratio is 1.5~1.2:1, and the reaction solvent is methanol, ethanol or tetrahydrofuran;

[0021] S2: Next, selenium dioxide is used to oxidize stable isotope-labeled 2-methyl-quinoxaline to form stable isotope-labeled 2-formaldehydequinoxaline; selenium dioxide and stable isotope-labeled 2-methylquinoxaline The molar ratio is 1.5~2.0:1, and the reaction solvent is 1,4-dioxane, ethyl acetate or tetrahydrofuran;

[0022] S3: Finally, the stable isotope-labeled 2-formaldehydequinoxaline is reacted with an oxidizing agent to obtain stable isotope-labeled quinoxaline-2-carboxylic acid; The ratio is 1.5-2.0:1, the oxidizing agent is hydrogen peroxi...

Embodiment 1

[0028] S1) After dissolving 1.12g of stable isotope-labeled o-phenylenediamine in 20mL of methanol, 2.7g of 40% aqueous solution of aceglyoxal was added dropwise, and reacted at 40°C for 24 hours. After cooling to room temperature, 80 mL of ethyl acetate was added, followed by washing with 1M hydrochloric acid (30 mL), water (30 mL) and saturated brine. After drying over anhydrous sodium sulfate, filter, remove the solvent under reduced pressure, and separate and purify by column chromatography. The eluent was selected to elute the product with n-hexane:ethyl acetate=6:1. Finally, 1.19 g of stable isotope-labeled 2-methylquinoxaline was obtained as an orange oily liquid with a yield of 80.1%.

[0029] S2) Dissolve 1.19 g of the stable isotope-labeled 2-methylquinoxaline obtained above in 50 mL of 1,4-dioxane, then add 1.35 g of selenium dioxide, and react at 100 degrees for 4 hours. After the reaction, cool down, remove the solid by suction filtration, remove part of the sol...

Embodiment 2

[0032] S1) After dissolving 1.68g of stable isotope-labeled o-phenylenediamine in 20mL of ethanol, 3.24g of 40% aqueous solution of methylglyoxal was added dropwise, and reacted at 60°C. React for 12 hours. After the end, the aftertreatment was the same as step (1) in Example 1 to obtain 1.84 g of stable isotope-labeled 2-methylquinoxaline, with a yield of 83.3%.

[0033] S2) Dissolve the stable isotope-labeled 2-methylquinoxaline obtained above in 60 mL of ethyl acetate, then add 2.68 g of selenium dioxide, and react at 80 degrees for 4.5 hours. After the reaction was completed, it was cooled to room temperature, and the aftertreatment was the same as step S2) in Example 1 to obtain 1.63 g of the target product with a yield of 81.1%.

[0034] S3) The stable isotope-labeled 2-formaldehydequinoxaline obtained above was dissolved in 30 mL of N,N-dimethylformamide, and 6.14 g of potassium hydrogen persulfate was added to react at room temperature for 2 hours. After the reaction...

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Abstract

The invention discloses a synthesis method of stable isotope labeled quinoxaline-2-carboxylic acid. The method comprises the following steps: S1: carrying out a condensation reaction on a methylglyoxal water solution and stable isotope labeled aniline to obtain stable isotope labeled 2-methylquinoxaline; S2, oxidizing the stable isotope labeled 2-methylquinoxaline by using selenium dioxide to formstable isotope labeled 2-formaldehyde quinoxaline; and S3, finally, enabling the stable isotope labeled 2-formaldehyde quinoxaline to react with an oxidizing agent, so as to obtain the stable isotopelabeled quinoxaline-2-carboxylic acid. According to the synthesis method of the stable isotope labeled quinoxaline-2-carboxylic acid, the purity of the prepared quinoxaline-2-carboxylic acid is 98% or above, and the isotope abundance is 99% or above; the reaction route is novel in design, mild in experimental conditions and high in yield; and the stable isotope labeled quinoxaline-2-carboxylic acid can be used as an internal standard substance for detecting quinoxaline veterinary drug residues, so that detection cost is greatly reduced.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing stable isotope-labeled quinoxaline-2-carboxylic acid. Background technique [0002] Quinoxaline compounds are a class of substances with a quinoxaline-N,N-dioxide structure. Studies have found that this type of substance has a good broad-spectrum antibacterial effect, and is particularly sensitive to Gram-negative bacteria, so it can be used as an antibiotic, such as carbadox. Not only that, but in actual use, many quinoxaline derivatives also have the functions of protein assimilation, promoting livestock growth and improving feed conversion rate, such as olaquindox. Based on this, such substances have been widely used in feed additives. However, with further research and development, researchers have found that such compounds are very easy to accumulate in organisms, and the products after being metabolized by organisms have obvious toxi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/44
CPCC07D241/44C07B2200/05
Inventor 陈武炼邓晓军赵超敏
Owner PLANTS & ANIMALS & FOOD TESTING QUARANTINE TECH CENT SHANGHAI ENTRY EXIT INSPECTION & QUARANTINE BUREAU
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