A kind of synthetic method of nitramide

A synthesis method and technology of nitramide, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of poor stability, many reaction steps, high price, etc., and achieve high synthesis efficiency, high conversion rate, selective effect

Active Publication Date: 2021-02-19
NORTHWEST UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0008] The above two reaction conditions have limitations such as more reaction steps (the first method) and the use of more complicated nitrosating reagents (the first and second methods). It is a problem worth studying to prepare the target product while avoiding the use of expensive nitrosating reagents and poorly stable Grignard reagents.

Method used

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  • A kind of synthetic method of nitramide
  • A kind of synthetic method of nitramide
  • A kind of synthetic method of nitramide

Examples

Experimental program
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Effect test

Embodiment 1

[0029]

[0030] A kind of synthesis of N-methyl-N-phenyl nitramide:

[0031] ① Add 2.14g of N-methylaniline to a 50mL round bottom flask, add 25mL of acetonitrile, stir at room temperature to dissolve;

[0032] ② Slowly add 5.22 g of nitropyridinium salt to the reaction system in batches, and the ratio of the amount of substrate N-methylaniline to the nitropyridinium salt of the nitrating agent is 1:1.5;

[0033] ③React directly in an air atmosphere, mix well at room temperature, slowly heat to 50°C, monitor the progress of the reaction with thin-layer chromatography, react at 0.1MPa for 6 hours, the raw materials are completely converted, stop the reaction, and cool to room temperature;

[0034] ④Add 50mL saturated NaHCO to the system 3 solution, then add 50mL dichloromethane solution, shake, separate liquid, extract the aqueous phase with dichloromethane three times, 30mL each time, combine the organic phase, wash twice with saturated brine, 10mL each time, and concentra...

Embodiment 2

[0038]

[0039] A kind of synthesis of N-nitroindoline:

[0040] ① Add 2.38g of indoline to a 50mL round bottom flask, add 25mL of acetonitrile, stir at room temperature to dissolve;

[0041] ② Slowly add 4.18g of nitropyridinium salt to the reaction system in batches, and the ratio of the amount of substrate indoline to the nitropyridinium salt of the nitrating agent is 1:1.2;

[0042] ③React directly in the air atmosphere, mix well at room temperature, slowly heat to 40°C, monitor the progress of the reaction with thin-layer chromatography, react at 0.1MPa for 4.5h, the raw materials are completely converted, stop the reaction, and cool to room temperature;

[0043] ④Add 50mL saturated NaHCO to the system 3 solution, then add 50mL dichloromethane solution, shake, separate liquid, extract the aqueous phase with dichloromethane three times, 30mL each time, combine the organic phase, wash twice with saturated brine, 10mL each time, and concentrate on a rotary evaporator to ...

Embodiment 3

[0047]

[0048] A kind of synthesis of N-nitro-1,2,3,4-tetrahydroquinoline:

[0049] ① Add 2.66g of 1,2,3,4-tetrahydroquinoline into a 50mL round bottom flask, add 25mL of acetonitrile, stir at room temperature to dissolve;

[0050] ② Slowly add 4.52 g of nitropyridinium salt to the reaction system in batches, and the ratio of the amount of substrate 1,2,3,4-tetrahydroquinoline to the nitropyridinium salt of the nitrating agent is 1: 1.3;

[0051] ③React directly in an air atmosphere, mix well at room temperature, slowly heat to 50°C, monitor the progress of the reaction with thin-layer chromatography, react at 0.1MPa for 7 hours, the raw materials are completely converted, stop the reaction, and cool to room temperature;

[0052] ④Add 50mL saturated NaHCO to the system 3 solution, then add 50mL dichloromethane solution, shake, separate liquid, extract the aqueous phase with dichloromethane three times, 30mL each time, combine the organic phase, wash twice with saturated ...

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Abstract

A method for synthesizing nitramide, comprising reacting an aniline reaction substrate with a nitrating agent in a solvent for 2 to 8 hours at 20 to 60°C to obtain nitramide; wherein, the aniline reaction substrate is N-methylaniline , indoline or 1,2,3,4‑tetrahydroquinoline. The method of the invention has the advantages of simple treatment and operation, high conversion rate and good selectivity. Products based on indoline and 1,2,3,4-tetrahydroquinoline can be separated and purified by column chromatography; the nitroamide product based on N-methylaniline can be directly purified in solution due to its low stability. To characterize.

Description

technical field [0001] The invention relates to the fields of organic synthesis and fine organic chemistry, in particular to a method for synthesizing nitroamide. Background technique [0002] Nitroamine (Nitroamine) compounds refer to compounds containing nitro and amine bonds and effects in the molecule, which can be converted into corresponding hydrazine compounds through reduction, and then undergo a series of transformations (E.J.Corey, et.al.Journal of the American Chemical Society, 1970, 92(8), 2476; B.-C.Feng, et.al.Qingdao KejiDaxue Xuebao, Ziran Kexueban, 2003, 24(4), 297; M.A.Wilson, et.al.U.S.Pat.Appl .Publ.US 20080027090; T.Kiyoi, et.al.Bioorganic & Medicinal Chemistry Letters, 2010, 20(16), 4918. etc.). Therefore, nitroamide compounds are important intermediates and building blocks in organic synthesis and fine organic chemistry. In this compound, N–NO 2 Bond construction is a key step in synthesis. [0003] For N-methyl-N-phenylnitramide compounds, there a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08C07D215/58C07C241/00C07C243/02
CPCC07C241/00C07D209/08C07D215/58C07C243/02
Inventor 焦林郁殷晓美张泽宁资慧洪乾马晓迅孙鸣李卓
Owner NORTHWEST UNIV
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