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Synthesis process of 4-trifluoromethyl nicotinic acid

A technology of trifluoromethyl nicotinic acid and synthesis process, applied in the direction of organic chemistry and the like, can solve the problems of high production cost and high raw material cost, and achieve the effects of low equipment requirements, simple operation and high total yield

Inactive Publication Date: 2018-01-26
SHANGHAI HETENG FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But in this method, the ring-closing yield is only 45.3%
And its raw material cost is too high, and production cost is huge

Method used

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  • Synthesis process of 4-trifluoromethyl nicotinic acid
  • Synthesis process of 4-trifluoromethyl nicotinic acid
  • Synthesis process of 4-trifluoromethyl nicotinic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 12.9g (323.5mmol) of NaH (323.5mmol) and 150g of DMF into the reaction flask under the protection of nitrogen at -15~-10°C, and slowly add 4-amino-1,1,1-trifluoro-3-buten-2-one dropwise under stirring 50g (359.5mmol) solution, the system turned from colorless to light yellow and finally to red suspension, 41.75g ​​(359.5mmol) of methyl 3-methoxyacrylate was added dropwise and reacted at this temperature for 3 hours.

[0029] Add concentrated hydrochloric acid dropwise to the reaction flask at -10°C to adjust the pH to 8-9, the system turns from dark red suspension to orange yellow, add 1.5L of water and at the same time dilute hydrochloric acid to adjust the pH to 1-2, a large amount of white flocculent solids precipitate out, stir for 0.5 hours and filter to obtain White product 81.5g (yield 88.3%).

[0030] Carry out nuclear magnetic resonance analysis to the product obtained in the present embodiment, see figure 1 The spectrum shown proves that the obtained prod...

Embodiment 2

[0032] Add 7.76g (194.1mmol) of NaH (194.1mmol) and 90g of DMF into the reaction bottle under the protection of nitrogen at -15~-10°C, slowly add 4-amino-1,1,1-trifluoro-3-buten-2-one dropwise under stirring 30g (215.7mmol) and 25g (215.7mmol) of methyl 3-methoxyacrylate were mixed solution, reacted at this temperature for 3h. The system turned from colorless to light yellow and finally to a red suspension, and reacted at this temperature for 3 hours.

[0033] Add concentrated hydrochloric acid dropwise to the reaction bottle at -10°C to adjust the pH to 8-9, the system turns from dark red suspension to orange yellow, add 1L of water and at the same time dilute hydrochloric acid to adjust the pH to 1-2, a large amount of light yellow flocculent solid precipitates, stir for 0.5 hours and filter to obtain 45.2 g of light yellow product (yield 82.1%).

[0034] NMR analysis of the product obtained in this example proved that the product obtained was N-1-methoxy-2-methoxycarbonyle...

Embodiment 3

[0036] Under nitrogen protection, add 5.18g (129.4mmol) of NaH (129.4mmol) and 60g of DMF into the reaction flask at -15~-10°C and add 16.7g (143.8mmol) of 3-methoxymethyl acrylate dropwise under stirring, then slowly add 4-amino -1,1,1-Trifluoro-3-buten-2-one 20g (143.8mmol) solution, reacted at this temperature for 3 hours. The system turned from colorless to light yellow and finally to a red suspension, and reacted at this temperature for 3 hours.

[0037] Add concentrated hydrochloric acid dropwise to the reaction bottle at -10°C to adjust the pH to 8-9, the system turns from dark red suspension to orange yellow, add 0.5L of water and at the same time dilute hydrochloric acid to adjust the pH to 1-2, a large amount of light yellow flocculent solid precipitates, stir for 0.5 hours After filtration, 28.7 g (yield: 78.2%) of a pale yellow product was obtained.

[0038] NMR analysis of the product obtained in this example proved that the product obtained was N-1-methoxy-2-met...

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Abstract

The invention discloses a novel synthesis process of 4-trifluoromethyl nicotinic acid. N-1-methoxy-2-methoxycarbonyl ethyl-4,4,4-trifluoro-3-one-1-butene amine is prepared from 4-amino-1,1,1-trifluoro-3-butene-2-one, and 4-trifluoromethyl nicotinic acid is obtained in a high-yield manner through one-pot ring closing hydrolysis under the action of alkali. The method can meet the industrial mass production demands due to unique novelty, higher total yield, low cost, simplicity in operation and lower equipment requirements.

Description

technical field [0001] The invention relates to a method for synthesizing chemical products, in particular to a process for synthesizing 4-trifluoromethylnicotinic acid. Background technique [0002] 4-Trifluoromethylnicotinic acid is an important pharmaceutical and pesticide intermediate, which is widely used in the creation of new pesticides. In terms of finished drugs, the most notable example is as an important synthetic raw material for the pesticide flonicamid. Currently, there are several reports on the synthesis of 4-trifluoromethylnicotinic acid: [0003] The patent with the publication number CN 101851193 A once reported a method. It is worth mentioning that the legal status of the patent is "deemed withdrawn after the publication of the invention patent application". In the patent report, 2,6-dichloro The description of the physical and chemical properties of -3-cyano-4-trifluoromethylpyridine is inconsistent with the facts, and the reaction yield of this step is...

Claims

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Application Information

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IPC IPC(8): C07D213/80C07D213/803
Inventor 陈盛施冠成孟海成
Owner SHANGHAI HETENG FINE CHEM
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