Synthesis method of 4-aminoquinaldine

A synthesis method, quinaldine technology, applied in the field of synthesis of 4-aminoquinaldine, can solve the problems of high risk and inconvenient operation, and achieve the effect of simple raw materials, simple operation, and simple separation and purification method

Inactive Publication Date: 2018-08-10
北京凯恩梅格医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This route involves high-temperature melting reaction and high-pr

Method used

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  • Synthesis method of 4-aminoquinaldine
  • Synthesis method of 4-aminoquinaldine
  • Synthesis method of 4-aminoquinaldine

Examples

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Embodiment 1

[0050] The synthetic method of existing 4-aminoquinaldine:

[0051]

[0052] ①Put 45.5ml (0.5mol) of double-distilled aniline, 137.0ml (0.7mol) of ethyl acetoacetate, 196ml of benzene and 2.0ml (0.01mol) of acetic acid into a 500mL three-necked bottle, heat and reflux until the water separator is free. Water brought out. After recovery of benzene under normal pressure, the low boilers are recovered by distillation under reduced pressure, and the residual liquid is the crude product of ethyl β-aniline crotonate (I), which is a light brown-red liquid, about 100 mL.

[0053] ②In a 500ml three-necked round bottom flask equipped with a dropping funnel, a sealed stirrer and an air condenser, place 120ml of the pilot oil, stir and heat to reflux. At the same time, 100ml of the obtained liquid (I) was quickly added, continued to stir and reflux for about 9 minutes, and cooled to room temperature. Add an appropriate amount of petroleum ether (60-90°C), and leave it overnight to pr...

Embodiment 2

[0058] 1. Synthesis of 2-methylquinoline N-oxide

[0059]

[0060] 143.1 g (1 mol) of 2-methylquinoline was dissolved in 1000 ml of acetic acid, and 300 ml of hydrogen peroxide (30%) was added, then heated to 80° C. and stirred for 4-5 hours.

[0061] Track the progress of the reaction with a thin layer of silica gel, developer: ethyl acetate, until the reaction is complete. Evaporate the acetic acid under reduced pressure, dissolve the residue in water, add an equal volume of dichloromethane and stir, separate the dichloromethane layer, dry it with anhydrous sodium sulfate, concentrate and separate by column (pure ethyl acetate) to obtain 2-methylquinoline N-oxide, light yellow solid crude product 156g, yield 98%. Proceed directly to the next reaction.

[0062] 2. Synthesis of 2-methyl-4-nitroquinoline N-oxide

[0063]

[0064] Dissolve 76g (0.48mol) of 2-methyl-4-nitroquinoline N-oxide in 507ml of nitric acid, add 101ml of sulfuric acid (the solution is dark red and...

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Abstract

The invention relates to a synthesis method of 4-aminoquinaldine. The invention discloses the synthesis method of the 4-aminoquinaldine; the method comprises the following steps: enabling 2-methyl quinoline, taken as a starting raw material, to be subjected to a hydrogen peroxide oxidation reaction in acetic acid so as to generate 2-methylquinoline N-oxide; then, carrying out a nitration reactionto generate 2-methyl-4-nitroquinoline N-oxide; after that, illuminating for carrying out a reaction to generate 2-methyl-4-nitroquinoline; producing 2-methyl-4-aminoquinoline N-oxide by means of interaction of ferric trichloride hexahydrate and hydrazine hydrate in ethanol; finally, carrying out a reduction reaction by using iron powder under the action of acetic acid so as to generate the 4-aminoquinaldine. The synthesis method provided by the invention has the beneficial effects that the used raw materials and reagents are low in price and easy to obtain, the synthesis method is simple and feasible, the reaction conditions are mild, and a simple and convenient synthetic route is opened up to the synthesis of the 4-aminoquinaldine.

Description

technical field [0001] The invention belongs to the fields of chemical industry and chemical medicine, and in particular relates to a synthesis method of 4-aminoquinaldine. Background technique [0002] Quinoline rings are a class of heterocycles with strong biological activity. Quinoline drugs are widely used in the prevention and treatment of diseases such as ulcers, malaria, and schizophrenia. They also have antifungal, anti-tuberculosis, and anti-filariasis properties. Certain compounds have been commercialized, such as quinine and chloroquine, which were earlier used by humans to prevent and treat malaria, and have been used to this day. Saquinavir is the first protease inhibitor marketed for the treatment of AIDS; aripiprazole is suitable for the treatment of various acute and chronic schizophrenia and schizoaffective disorder. Many small molecule drugs can also improve their physiological activity and enhance drug efficacy through quinoline group modification. In pe...

Claims

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Application Information

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IPC IPC(8): C07D215/42C07D215/60C07D215/18
CPCC07D215/18C07D215/42C07D215/60
Inventor 刘晶晶吴弼东
Owner 北京凯恩梅格医药科技有限公司
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