A method for synthesizing 2-halogenonicotinic acid ester and 2-halogenonicotinic acid by hydrothermal method
A technology of halogenated nicotinic acid ester and hydrothermal method, which is applied in the direction of organic chemistry, can solve the problems of long reaction time, difficult handling, general product yield, etc., and achieve the effect of shortening the reaction time
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Embodiment 1
[0031] Embodiment one (synthesis of methyl 2-chloronicotinate):
[0032] N,N-dibutylaminoacrolein 69mL (0.5mol), TiO 2 Add 0.3g, 10.0g of tetrabutylammonium hydroxide and 50mL of deionized water into the hydrothermal reactor, then add 65mL (0.6mol) of methyl cyanoacetate and mix well, and react under hydrothermal method at 90°C and 0.3MPa nitrogen for 0.25h. Filter after the reaction is over, extract with 90 g of n-hexane, add dry HCl gas to the organic phase for reaction, TLC (developed with ethyl acetate, observe under ultraviolet light) follow the reaction until the end of the reaction, add 30% trimethylamine in the reaction solution Adjust the pH value of the aqueous solution to neutral, separate the liquids to obtain the organic phase, distill off the solvent under reduced pressure (recovery and apply it mechanically), and rectify the residue under reduced pressure, collect 110-115°C / 1mmHg fractions to obtain methyl 2-chloronicotinate Colorless liquid, the content of me...
Embodiment 2
[0037] Embodiment two (synthesis of methyl 2-bromonicotinate):
[0038] Add 61mL (0.5mol) of 3-diethylaminoacrolein, 6.5g of copper powder, 10.0g of triethylbenzyl ammonium chloride and 50mL of deionized water into the hydrothermal reactor, and then add 65mL of methyl cyanoacetate (0.6mol) and mix well, react by hydrothermal method at 100°C and nitrogen 3MPa for 0.5h, filter after the reaction, extract with 120g cyclohexane, and then pass the organic phase into dry HBr gas for reaction, TLC (developed with ethyl acetate, UV Observation under the lamp) Follow the reaction until the end of the reaction, add 40% dimethylamine lye in the reaction solution to adjust the pH value to neutral, separate the liquids to obtain an organic phase, wash with water, dry over anhydrous sodium sulfate, filter, and remove under reduced pressure The solvent (recovered and used mechanically) was used to obtain methyl 2-bromonicotinate as a light brown liquid, the content of methyl 2-bromonicotinat...
Embodiment 3
[0041] Embodiment three (synthesis of ethyl 2-chloronicotinate):
[0042]Add 69mL (0.5mol) of N,N-dibutylaminoacrolein, 6.5g of CuO, 10.0g of trimethyldodecylammonium bromide and 50mL of deionized water into the hydrothermal reactor, and then add cyano Ethyl acetate 65mL (0.6mol) was mixed, and reacted by hydrothermal method at 110°C and 0.25MPa nitrogen for 0.3h. After the reaction was completed, it was filtered, extracted with 220g of xylene, and the organic phase was reacted with dry HCl gas. TLC (ethyl acetate Ester development, observation under ultraviolet light) follow the reaction until the end of the reaction, add 40% ammonium bicarbonate by mass content in the reaction solution to adjust the pH value to neutral, separate the liquids to obtain the organic phase, evaporate the solvent under reduced pressure (recovery and apply mechanically), and the residue Vacuum rectification, collecting fractions at 110-115°C / 1mmHg to obtain a colorless liquid of 2-chloronicotinic a...
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