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Synthesis method of 5-aminolevulinic acid hydrochloride

A technology of aminolevulinic acid hydrochloride and synthesis method, which is applied in chemical instruments and methods, preparation of carboxylic acid esters, preparation of organic compounds, etc., can solve the problem that ethyl bromoacetoacetate is highly polluting to the environment and is not suitable for large-scale industrialization Low production and reaction yields, etc., achieve the effect of low synthesis cost, less three wastes, and easy access to raw materials

Active Publication Date: 2019-01-25
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction method step is loaded down with trivial details, and reaction yield is low, and ethyl bromoacetoacetate is bigger to environmental pollution, is not suitable for a large amount of industrialized production:

Method used

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  • Synthesis method of 5-aminolevulinic acid hydrochloride
  • Synthesis method of 5-aminolevulinic acid hydrochloride
  • Synthesis method of 5-aminolevulinic acid hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The synthesis of 5-aminolevulinic acid hydrochloride comprises the following steps:

[0043] Step 1: Synthesis of Monomethyl Succinate

[0044] Dry methanol (112.14 g, 3500 mmol) was added to a 500 mL single-necked flask, and succinic anhydride (100.07 g, 1000 mmol) was added to the single-necked flask under magnetic stirring. After the raw materials were added, the temperature was raised to 80°C, heated to reflux, and reacted for 3 hours. After the reaction, the reaction solution was in a clear state. The reaction solution was distilled under reduced pressure (using a water pump to carry out vacuum distillation), methanol was distilled off, the remaining liquid was cooled to room temperature, crystallized overnight, and a white solid was obtained by suction filtration the next day, which was Monomethyl succinate, yield 97%.

[0045] Step 2: Synthesis of methyl 4-(1-imidazole)-4-oxobutanoate

[0046] Add dry dichloromethane (400 mL) into a 2000 mL three-necked flask,...

Embodiment 2

[0052] The synthesis of 5-aminolevulinic acid hydrochloride comprises the following steps:

[0053] Step 1: Synthesis of Monomethyl Succinate

[0054] Dry methanol (128.17g, 4000mmol) was added to a 500mL single-necked flask, and succinic anhydride (100.07g, 1000mmol) was added to the single-necked flask under magnetic stirring. After the raw materials were added, the temperature was raised to 75°C, heated to reflux, and reacted for 5 hours. After the reaction, the reaction solution was in a clear state. The reaction solution was distilled under reduced pressure (using a water pump to carry out vacuum distillation), methanol was distilled off, the remaining liquid was cooled to room temperature, crystallized overnight, and a white solid was obtained by suction filtration the next day, which was Monomethyl succinate, yield 96%.

[0055] Step 2: Synthesis of methyl 4-(1-imidazole)-4-oxobutanoate

[0056] Add dry tetrahydrofuran (400 mL) into a 2000 mL three-necked flask, stir...

Embodiment 3

[0062] The synthesis of 5-aminolevulinic acid hydrochloride comprises the following steps:

[0063] Step 1: Synthesis of Monomethyl Succinate

[0064] Dry methanol (144.19 g, 4500 mmol) was added to a 500 mL single-necked flask, and succinic anhydride (100.07 g, 1000 mmol) was added to the single-necked flask under magnetic stirring. After the raw materials were added in, the temperature rose to 78°C, heated to reflux, and reacted for 4 hours. After the reaction, the reaction solution was in a clear state. The reaction solution was distilled under reduced pressure (using a water pump to carry out vacuum distillation), methanol was distilled off, the remaining liquid was cooled to room temperature, crystallized overnight, and a white solid was obtained by suction filtration the next day, which was Monomethyl succinate, yield 95%.

[0065] Step 2: Synthesis of methyl 4-(1-imidazole)-4-oxobutanoate

[0066] Add dry dichloroethane (400 mL) into a 2000 mL three-necked flask, sti...

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Abstract

The invention relates to a synthesis method of 5-aminolevulinic acid hydrochloride. The method includes the steps that succinic anhydride is used as the raw material and subjected to monoesterification with methanol to obtain monomethyl succinate; monomethyl succinate and N,N-carbonyldiimidazole are subjected to a nucleophilic substitution reaction to obtain methyl 4-(1-imidazole)-4-oxobutanoate;methyl 4-(1-imidazole)-4-oxobutanoate and nitromethane are subjected to a nucleophilic substitution reaction under the catalysis of an alkali compound to obtain methyl 5-nitro-4-oxopentanoate; methyl5-nitro-4-oxopentanoate and a metallic reducing agent are subjected to a reduction reaction, and through hydrolysis, 5-aminolevulinic acid hydrochloride is obtained. The process is simple, the raw material is easy to obtain, no special rectification and recrystallization devices are needed for treating intermediate products, no toxic and expensive raw materials are used, the use of heavy metal reducing agents is avoided to prevent environmental pollution, the synthesis cost is low, the purity of the synthetic product can reach 97% in recrystallization detection, and the total yield is high andreaches 70% or above.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a synthesis method of 5-aminolevulinic acid hydrochloride. Background technique [0002] 5-Aminolevulinic acid hydrochloride, also known as 5-amino-4-oxopentane hydrochloride, δ-aminopentanone hydrochloride, is widely used in the fields of medicine and pesticides. First of all, 5-aminolevulinic acid hydrochloride, as a new type of photodynamic therapy drug, can be used for the treatment of local or systemic skin cancer; it also has certain curative effects on bladder cancer, lung cancer, and digestive tract cancer. Secondly, in the field of pesticides, 5-aminolevulinic acid hydrochloride can be used as a selective herbicide, insecticide and plant growth regulator in agriculture, which can promote plant growth, increase yield, enhance stress resistance, and improve fruit quality, etc. , has broad application prospects. Therefore, it is very necessary to find an environm...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/40C07D233/60C07C201/12C07C205/51C07C227/04C07C229/22
CPCC07C67/08C07C201/12C07C227/04C07D233/60C07C69/40C07C205/51C07C229/22
Inventor 徐元清夏强强徐浩甘信燃丁涛刘保英张文凯王延鹏任艳蓉房晓敏
Owner HENAN UNIVERSITY
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