Synthetic method of N-((2-(1,3-dioxo-dihydroisoindol-2-yl)-propionyl)-5-methoxy)formamide

A technology of dioxoisoindoline and synthesis method, applied in the direction of organic chemistry and the like, can solve problems such as unfavorable industrialization promotion, time-consuming, low yield, etc. The effect of activation energy

Active Publication Date: 2016-06-15
ITIC MEDCHEM CO LTD
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0007] The method yield is low, the synthesis process takes a long time, and the energy consumption is high, which is unfavorable for industrialization promotion

Method used

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  • Synthetic method of N-((2-(1,3-dioxo-dihydroisoindol-2-yl)-propionyl)-5-methoxy)formamide
  • Synthetic method of N-((2-(1,3-dioxo-dihydroisoindol-2-yl)-propionyl)-5-methoxy)formamide
  • Synthetic method of N-((2-(1,3-dioxo-dihydroisoindol-2-yl)-propionyl)-5-methoxy)formamide

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Experimental program
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Effect test

Embodiment 1

[0035] A method for synthesizing N-(2-(1,3-dioxoisoindolin-2-yl)-propionyl)-5-methoxy)formamide, comprising the following steps:

[0036] Step 1: Dissolve 11.9mmol of 2-nitro-4-methoxyaniline in 20mL concentrated sulfuric acid solution (mass concentration is 70%), reduce the temperature of the system to -5℃, set the temperature to 0℃ and the concentration to 2mol 10mL of sodium nitrite solution was quickly added to the vigorously stirred reaction system, and reacted at 0°C for 10 minutes; the reaction system was poured into 5mL of sodium iodide solution with a temperature of 0°C and a concentration of 4mol / L. Continue to react for 30 minutes;

[0037] The filtered residue was washed with 6N hydrochloric acid and water, and the crude product was crystallized in n-hexane to obtain a yellow solid A;

[0038] Step 2: Add 8.4mmol of bromopropyne and 8.4mmol of potassium phthalimide to 10mL of N,N-dimethylformamide, then add 0.2g of solid manganese dioxide, and react at 28°C 1h;

[0039] ...

Embodiment 2

[0047] A method for synthesizing N-(2-(1,3-dioxoisoindolin-2-yl)-propionyl)-5-methoxy)formamide, comprising the following steps:

[0048] The first step: Dissolve 11.9mmol of 2-nitro-4-methoxyaniline in 20mL concentrated sulfuric acid solution (mass concentration of 71%), reduce the system temperature to -5℃, set the temperature to 0℃ and the concentration to 2mol 10mL of sodium nitrite solution was quickly added to the vigorously stirred reaction system, and reacted at 0℃ for 15min; the reaction system was poured into 5mL of sodium iodide solution with a temperature of 0℃ and a concentration of 4mol / L. Continue to react for 30 minutes;

[0049] The filtered residue was washed with 6N hydrochloric acid and water, and the crude product was crystallized in n-hexane to obtain a yellow solid A;

[0050] Step 2: Add 8.4mmol of bromopropyne and 8.4mmol of potassium phthalimide to 10mL of N,N-dimethylformamide, then add 0.3g of solid manganese dioxide, and react at 28°C 2h;

[0051] Add 10...

Embodiment 3

[0059] A method for synthesizing N-(2-(1,3-dioxoisoindolin-2-yl)-propionyl)-5-methoxy)formamide, comprising the following steps:

[0060] Step 1: Dissolve 11.9mmol of 2-nitro-4-methoxyaniline in 20mL concentrated sulfuric acid solution (mass concentration is 70%), reduce the temperature of the system to -5℃, set the temperature to 0℃ and the concentration to 2mol 10mL of sodium nitrite solution was quickly added to the vigorously stirred reaction system, and reacted at 0℃ for 15min; the reaction system was poured into 5mL of sodium iodide solution with a temperature of 0℃ and a concentration of 4mol / L. Continue to react for 30 minutes;

[0061] The filtered residue was washed with 6N hydrochloric acid and water, and the crude product was crystallized in n-hexane to obtain a yellow solid A;

[0062] Step 2: Add 8.4mmol of bromopropyne and 8.4mmol of potassium phthalimide to 10mL of N,N-dimethylformamide, then add 0.2g of solid manganese dioxide, and react at 28°C 2h;

[0063] Add 100...

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Abstract

The invention discloses a synthetic method of N-(2-(1,3-dioxo-dioxoisoindolin-2-yl)-propionyl)-5-methoxy)formamide. 2-nitro-4-anisidine is taken as an initial raw material, 2-iodine-3-methoxy nitrobenzene is obtained by substitution reaction on a diazonium salt aromatic ring, and then the 2-iodine-3-methoxy nitrobenzene and propargylamine are subjected to Castro-Stephens coupling reaction, reduction reaction and acylation reaction to obtain the N-(2-(1,3-dihydroisoindol-2-yl)-propionyl)-5-methoxy)formamide. Reaction conditions are optimized based on the prior art, and concentrated sulfuric acid replaces concentrated nitric acid; manganese dioxide solid is adopted to catalyze the reaction of propargyl bromide and phthalimide kali salt; manganous-manganic oxide is adopted as a catalyst to catalyze and promote the reaction together with triethylamine, bispalladium chloride and cuprous iodide, the reaction efficiency and yield of a final product are improved, and the industrial production and promotion of the N-(2-(1,3-dioxo-dihydroisoindol-2-yl)-propionyl)-5-methoxy)formamide are facilitated.

Description

Technical field: [0001] The invention discloses a synthesis method of N-(2-(1,3-dioxoisoindolin-2-yl)-propionyl)-5-methoxy)formamide, which belongs to the technical field of organic synthesis . Background technique: [0002] Indole compounds are an important branch of heterocyclic compounds. They are the most widely distributed heterocyclic compounds in nature. They are important organic chemical raw materials and products with various physiological activities. As intermediates for pesticides, medicines, spices, dyes and other fine chemical products, indole compounds and their derivatives are more and more widely used. [0003] In recent years, indole compounds have sprung up and have gradually developed into the mainstream of new drug research and development. With its unique chemical structure, indole can synthesize antipyretic analgesics, stimulants, antihypertensive drugs, vasodilators, anti-resistive amines, etc. 4-Nitroindole is an important intermediate for the preparatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 胡海威丁靓闫永平郑辉严辉
Owner ITIC MEDCHEM CO LTD
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