2-phenylnicotinic acid derivatives with insecticidal and acaricidal activities
A technology of phenyl and alkyl, applied in the field of 2-phenylnicotinic acid derivatives
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Embodiment 1
[0222] Embodiment 1: the preparation of intermediate 6-methyl-(4-trifluoromethyl)-nicotinoyl chloride
[0223] 1) Preparation of 6-methyl-2-chloro-nicotinic acid ethyl ester
[0224]
[0225] Put 45.25g (0.25mol) of 6-methyl-2-hydroxy-nicotinic acid ethyl ester into a 1000mL single-necked flask, add 200mL oxalyl chloride to it, heat up to reflux, and react for 8h. After the reaction is monitored by TLC, remove under reduced pressure. Solvent, the residue was poured into water, solids were precipitated, filtered with suction, the filter cake was washed with water, and air-dried to obtain 36 g of khaki solids, yield: 73%.
[0226] 2) Preparation of 6-methyl-(4-trifluoromethyl)-nicotinic acid ethyl ester
[0227]
[0228] Put 17.7g (0.089mol) of 6-methyl-2-chloro-nicotinic acid ethyl ester into a 500mL single-necked flask, add 80mL of toluene to it, then add 12.3g (0.089mol) of potassium carbonate, and weigh 16.9 g (0.089mol) p-trifluorophenylboronic acid was put into it,...
Embodiment 2
[0235] Embodiment 2: the preparation of intermediate 6-methyl-(4-trifluoromethyl)-3-chloromethylpyridine
[0236] 1) Preparation of 6-methyl-(4-trifluoromethyl)-3-hydroxymethyl-pyridine
[0237]
[0238] Put 10.2g (0.033mol) of 6-methyl-(4-trifluoromethyl)-nicotinic acid into a 250mL three-neck flask, add anhydrous chloroform to it, dissolve it, and add 0.12mol of tetrahydro Aluminum lithium was reacted at room temperature for 3 hours. After the reaction was monitored by TLC, a small amount of water was added, and a large amount of white solid was precipitated. After suction filtration, the filtrate was dried and precipitated to obtain 8 g of crude product, which was used directly. Yield: 90%.
[0239] 2) Preparation of 6-methyl-(4-trifluoromethyl)-3-chloromethylpyridine
[0240]
[0241] Put 8g of 6-methyl-(4-trifluoromethyl)-3-hydroxymethyl-pyridine crude product into a 250mL three-necked flask equipped with a tail gas absorption device, add 100mL of thionyl chloride ...
Embodiment 3
[0242] Embodiment 3: the preparation of intermediate 6-methyl-5-nitrile group-(4-trifluoromethyl)-nicotinoyl chloride
[0243] 1) Preparation of 6-methyl-5-cyano-2-chloro-nicotinic acid ethyl ester
[0244]
[0245] Put 51.5 grams (0.25mol) of 6-methyl-5-cyano-2-hydroxy-nicotinic acid ethyl ester into a 1000mL single-necked flask, add 200mL oxalyl chloride to it, raise the temperature to reflux, react for 8h, and monitor the reaction by TLC After completion, the solvent was removed under reduced pressure, the residue was poured into water, solids were precipitated, filtered with suction, the filter cake was washed with water, and air-dried to obtain 50 g of a khaki solid, yield: 89%.
[0246] 2) Preparation of 6-methyl-5-cyano-(4-trifluoromethyl)-nicotinic acid ethyl ester
[0247]
[0248] Put 0.089mol 6-methyl-5-cyano-2-chloro-nicotinic acid ethyl ester into a 500mL single-necked flask, add 80mL toluene to it, then add 12.3g (0.089mol) potassium carbonate to it, and w...
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