Method for synthesizing 4-trifluoromethyl nicotinic acid
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A technology of trifluoromethyl nicotinic acid and dimethyl methoxymethylene malonate, which is applied in the direction of organic chemistry, can solve the problems of impossible industrialization, and achieve convenient post-processing, high feasibility, and equipment requirements low effect
Active Publication Date: 2017-10-27
JIANGSU JIANNONG PLANT PROTECTION CO LTD
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The disadvantage of this method is that the key step uses a strong base such as n-butyllithium, and the...
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Embodiment 1
[0031] In a 500ml flask, add 1-methylpyrrolidone 100mL, sodium hydride 2.9g, stir and cool down to 0°C, add dropwise 1,1,1-trifluoro-4-aminobutenone 10g, control the temperature at 10°C Next, after reacting for 1 hour, 12.5 g of dimethyl 2-methoxymethylenemalonate was added, and reacted for 4 hours. Then add 200 mL of methanol, heat to 65°C, react for 3 hours, add 300 grams of concentrated hydrochloric acid (30% wt), heat to boiling, reflux for 9 hours, distill methanol off, add 300 grams of ice water, filter, and use the filter cake Washed with water, dried to obtain 6.8g yellow solid, yield 49%, the nuclear magnetic data of yellow solid is 1 HNMR (400MHz, DMSO-d6): d7.86(d, J=5.2Hz, 1H), 8.97(d, J=5.2Hz, 1H), 9.06(s, 1H), 14.04(bs, 1H), according to NMR data determined that the yellow solid was 4-trifluoromethylnicotinic acid, and the purity of 4-trifluoromethylnicotinic acid in the yellow solid was analyzed to be 98.7%.
Embodiment 2
[0033]In a 500ml flask, add DMF120mL, potassium tert-butoxide 12.4g, stir and cool down to 0°C, add 12.8g of 1,1,1-trifluoro-4-aminobutenone dropwise, control the temperature below 10°C, and react After 1 hour, 16.8 g of dimethyl 2-methoxymethylenemalonate was added and reacted for 3-5 hours. Then add 250 mL of ethanol, heat to 80°C, react for 2-3 hours, add 300 grams of concentrated hydrochloric acid, heat to boil, reflux for 8-10 hours, distill off ethanol, add 350 grams of ice water, filter, and wash the filter cake with water. Dry, obtain 6.2g yellow solid, productive rate 35%, the NMR data of yellow solid is 1 HNMR (400MHz, DMSO-d6): d7.86(d, J=5.2Hz, 1H), 8.97(d, J=5.2Hz, 1H), 9.06(s, 1H), 14.04(bs, 1H), according to NMR data determined that the yellow solid was 4-trifluoromethylnicotinic acid, and the purity of 4-trifluoromethylnicotinic acid in the yellow solid was analyzed to be 99.1%.
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Abstract
The invention relates to a method for synthesizing 4-trifluoromethyl nicotinic acid, in particular to a method for synthesizing a key flonicamid intermediate 4-trifluoromethyl nicotinic acid. The method comprises the following steps: by taking 1,1,1-trifluoro-4-amino-butenone and dimethyl 2-methoxy-methylene malonate as raw materials, carrying out first-step reaction, namely carrying out reaction on 1,1,1-trifluoro-4-amino-butenone and dimethyl 2-methoxy-methylene malonate under the alkaline condition of a polar solvent, so that a first-step reaction system is obtained; carrying out second-step reaction, namely adding an alcoholic solvent into the first-step reaction system, and carrying out heating reaction, so that a second-step reaction system is obtained; and carrying out third-step reaction, namely adding acid solution into the second-step reaction system, and carrying out reaction, so that the 4-trifluoromethyl nicotinic acid is obtained. The method provided by the invention has the advantages of available raw materials, simple operation, low cost, less side reaction and high product purity and is applicable industrial production.
Description
technical field [0001] The invention belongs to the field of synthesis of pesticide intermediates, in particular to a method for synthesizing 4-trifluoromethylnicotinic acid, a key intermediate of flonicamid. Background technique [0002] Flunicamid is a nicotinamide insecticide, which is effective against various piercing-sucking mouthparts pests, and has good penetration, which can penetrate from plant roots to stems and leaves. The drug works by hindering the sucking action of the pests, and the pests stop sucking soon after ingesting the drug, and finally starve to death. The drug can prevent the stylet tissues of sucking pests such as aphids from inserting into plant tissues and take effect. It has insecticidal activity against both adults and larvae of aphids. Its mechanism of action is novel, and it has no cross-resistance with other insecticides currently on the market, and has low toxicity to bees. The International Insecticide Resistance Action Committee (IRAC) ...
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