Preparation method of 2,5-dimethoxyphenylacetic acid

A technology of dimethoxybenzene and dimethoxyphenyl, which is applied in the field of drug synthesis, can solve the problems of good safety, difficulty in meeting market demand, and high cost, and achieve an effect that is conducive to environmental protection

Active Publication Date: 2021-01-05
ASTATECH CHENGDU BIOPHARM CORP
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Problems solved by technology

Among them, drug therapy still plays a major role in clinical practice. Clinical studies have found that feretin has a positive effect on the treatment of PD, and at the same time has low toxicity and good safety. However, 2,5-dimethoxyphenylacetic acid is required in the synthesis of feredin As a starting material, a series of aryl acetic acid compounds are synthesized by the Willgerodt-Kindler method in the current report, and 2,5-dimethoxyphenylacetic acid is prepared by this method. The yield is low and the cost is high, so it is difficult to satisfy the market need

Method used

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  • Preparation method of 2,5-dimethoxyphenylacetic acid
  • Preparation method of 2,5-dimethoxyphenylacetic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A. Add 9.96g (0.07208mol) of 1,4-dimethoxybenzene, 13.47g (0.07568mol) of N-bromosuccinimide, AuCl 3 (0.003mmol), dichloromethane 80mL, the mixture was stirred and reacted at 25°C for 2 hours, 40mL of water was added to the reaction system and stirred for 30min, the liquid was separated, the aqueous phase was extracted once with 40mL of dichloromethane, the organic phase was combined, anhydrous sodium sulfate Dry, concentrate the organic phase under reduced pressure, concentrate the residue and distill under reduced pressure to obtain 15.3 g of colorless liquid 2-bromo-1,4-dimethoxybenzene, yield 98%, HPLC 98.2%;

[0026] B. Add 10.85g (0.05mol) of 2-bromo-1,4-dimethoxybenzene, 7.64g (0.05mol) of methyl bromoacetate, and CoCl 2 65mg (0.5mmol), 1.44g (0.06mol) of magnesium strips, 116mg (1mmol) of N,N,N',N'-tetramethylethylenediamine, 250mL of anhydrous tetrahydrofuran, stirred at 25°C under the protection of argon React for 2 hours, add saturated ammonium chloride sol...

Embodiment 2

[0031] A. Add 9.96g (0.07208mol) of 1,4-dimethoxybenzene, 14.11g (0.07928mol) of N-bromosuccinimide, AuCl 3 (0.003mmol), chloroform 80mL, the mixture was stirred and reacted at 30°C for 1.5 hours, 40mL of water was added to the reaction system and stirred for 30min, the liquid was separated, the aqueous phase was extracted once with 40mL of dichloromethane, the organic phase was combined, anhydrous sodium sulfate Dry, concentrate the organic phase under reduced pressure, concentrate the residue and distill under reduced pressure to obtain 15.17 g of colorless liquid 2-bromo-1,4-dimethoxybenzene, yield 97%, HPLC 98.2%;

[0032] B. Add 10.85g (0.05mol) of 2-bromo-1,4-dimethoxybenzene, 8.4g (0.055mol) of methyl bromoacetate, and CoCl 2 65mg (0.5mmol), 1.44g (0.06mol) of magnesium strips, 116mg (1mmol) of N,N,N',N'-tetramethylethylenediamine, 250mL of anhydrous tetrahydrofuran, stirred at 30°C under the protection of argon React for 3 hours, add saturated ammonium chloride solut...

Embodiment 3

[0037] A. Add 9.96g (0.07208mol) of 1,4-dimethoxybenzene, 15.39g (0.08649mol) of N-bromosuccinimide, AuCl 3 (0.003mmol), dichloromethane 80mL, the mixture was stirred and reacted at 20°C for 3 hours, 40mL of water was added to the reaction system and stirred for 30min, the liquid was separated, the aqueous phase was extracted once with 40mL of dichloromethane, the organic phase was combined, anhydrous sodium sulfate Dry, concentrate the organic phase under reduced pressure, concentrate the residue and distill under reduced pressure to obtain 15.24 g of colorless liquid 2-bromo-1,4-dimethoxybenzene, yield 97.5%, HPLC 98.2%;

[0038] B. Add 10.85g (0.05mol) of 2-bromo-1,4-dimethoxybenzene, 9.17g (0.06mol) of methyl bromoacetate, and CoCl 2 65mg (0.5mmol), 1.44g (0.06mol) of magnesium strips, 116mg (1mmol) of N,N,N',N'-tetramethylethylenediamine, 250mL of anhydrous tetrahydrofuran, stirred at 35°C under the protection of argon React for 3 hours, add saturated ammonium chloride ...

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Abstract

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of 2,5-dimethoxyphenylacetic acid, which comprises the following steps: A, adding 1,4-dimethoxybenzene, N-bromosuccinimide and a catalyst into a solvent to react, carrying out liquid separation and extraction on the reaction system, and simultaneously combining, drying and concentratingthe organic phase under reduced pressure, and finally, carrying out reduced pressure distillation to obtain the 2-bromo-1,4-dimethoxybenzene. B, under the protection of argon, taking the 2-bromo-1,4-dimethoxybenzene obtained in the step A, bromoacetate, a catalyst and a magnesium strip to react in a solvent, and then extracting, washing, drying and distilling the reaction products to obtain 2-(2,5-dimethoxyphenyl)methyl acetate; c, hydrolyzing the 2-(2,5-dimethoxyphenyl)methyl acetate obtained in the step B, and then carrying out suction filtration and drying on a reaction system to finally obtain 2,5-dimethoxyphenylacetic acid. The yield and the total yield of the 2,5-dimethoxyphenylacetic acid obtained by the method disclosed by the invention are both higher than those of the 2,5-dimethoxyphenylacetic acid synthesized by a WillegerdtKindler method.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of 2,5-dimethoxyphenylacetic acid. Background technique [0002] Parkinson's disease (Parkinson's disease, PD) is a common neurodegenerative disease, the main clinical symptoms are muscle tremors, stiffness, movement difficulties, body posture and motor balance disorders. Further development will also appear recognition, perception, memory impairment and obvious dementia. [0003] The main pathological feature of PD is the degeneration of dopaminergic neurons in the substantia nigra compacta, and the content of dopaminergic neurotransmitters in the striatum is significantly reduced. The cause of dopaminergic neuron degeneration is unknown so far. Genetics, infection, abnormal immune function, aging, and neurotoxins in vivo and in vitro all play a role in the pathogenesis of PD. Oxidative stress and mitochondrial dysfunction play a role...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C59/64
CPCC07C51/09C07C67/343C07C41/22C07C59/64C07C69/734C07C43/225Y02P20/584
Inventor 杜全海杜乐朱新安周强小红郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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