One-pot method for synthesizing N-methylnitrone compounds

A methyl nitrone and compound technology, applied in the directions of organic chemistry, oxime preparation, etc., can solve the problems of harsh reaction conditions, complex synthesis process and high synthesis cost, and achieve the effects of low synthesis cost, simple process and good product quality.

Inactive Publication Date: 2009-08-26
NORTHWEST NORMAL UNIVERSITY
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  • Description
  • Claims
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Problems solved by technology

[0004] At present, the synthetic method of N-methylnitrone compounds is first to reduce nitromethane under high-pressure conditions to generate N-methylhydroxylamine hydrochloride, and then make N-methylhydroxylamine hydrochloride and aromatic aldehyde This method requires two steps to obtain the target product. The synthesis process is relatively complicated, the reaction conditions are relatively harsh, the yield is low, the synthesis cost is high, and the operation is inconvenient.

Method used

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  • One-pot method for synthesizing N-methylnitrone compounds
  • One-pot method for synthesizing N-methylnitrone compounds
  • One-pot method for synthesizing N-methylnitrone compounds

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Experimental program
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Effect test

Embodiment 1

[0021] Embodiment 1: the synthesis of α-phenyl-N-methylnitrone

[0022] Nitromethane (2.66 g, 43.6 mmol) and zinc powder (2.95 g, 45.4 mmol) were added in a 250 ml round bottom flask, then 150 ml of 95% ethanol was added as a solvent, and the mixture was placed in an ice-water bath After being cooled to below 10°C, acetic acid (5.4 grams) was added dropwise to the reaction solution, and after 3 hours of reaction, benzaldehyde (2.3 grams, 21.8 mmol) was added to the reaction solution, heated directly to 65°C, and reflux reaction 3 After 1 hour, 2.71 g of the target product was obtained by column chromatography. Yield 92.2%.

[0023] Its reaction formula is as follows:

[0024]

[0025] Spectral data: 1 HNMR (400MHz, CDCl 3 ): δ (ppm): 3.88 (s, 3H, N-CH 3 ), 7.37 (s, 1H, C-H), 7.42 (d, J=2.4Hz, 2H, Ph-H), 7.43 (d, J=0.9Hz, 1H, Ph-H), 8.22 (dd, J=3.0 , 6.6Hz, 2H, Ph-H).

Embodiment 2

[0026] Embodiment 2: the synthesis of α-(4-methoxyphenyl)-N-methylnitrone

[0027] Nitromethane (2.66 g, 43.6 mmol) and zinc powder (2.95 g, 45.4 mmol) were added in a 250 ml round bottom flask, then 150 ml of 95% ethanol was added as a solvent, and the mixture was placed in an ice-water bath After cooling to below 10°C, acetic acid (5.4 grams) was added dropwise to the reaction solution, and after 3 hours of reaction, p-methoxybenzaldehyde (2.95 grams, 21.8 mmol) was added to the reaction solution and heated directly to 65°C , refluxed for 3 hours, and separated by column chromatography to obtain 3.4 g of the target product. Yield 94.4%.

[0028] Its reaction formula is as follows:

[0029]

[0030] Spectral data of the synthesized product: 1 HNMR (400MHz, CDCl 3 ): δ (ppm): 3.85 (s, 6H, OCH 3 , NCH 3 ), 6.94(d, J=8.8Hz, 2H, Ph-H), 7.29(s, 1H, CH), 8.21(d, J=8.8Hz, Ph-H).

Embodiment 3

[0031] Embodiment 3: the synthesis of α-(2-chlorophenyl)-N-methylnitrone

[0032] Nitromethane (2.66 g, 43.6 mmol) and zinc powder (2.95 g, 45.4 mmol) were added in a 250 ml round bottom flask, then 150 ml of 95% ethanol was added as a solvent, and the mixture was placed in an ice-water bath After being cooled to below 10°C, acetic acid (5.4 g) was added dropwise to the reaction solution, and after 3 hours of reaction, 2-chlorobenzaldehyde (3.05 g, 21.8 mmol) was added to the reaction solution, and directly heated to 65°C , refluxed for 2 hours, and separated by column chromatography to obtain 3.3 g of the target product, with a yield of 89.2%.

[0033] Its reaction formula is as follows:

[0034]

[0035] Spectral data: 1 HNMR (400MHz, CDCl 3 ): δ (ppm): 3.88 (s, 3H, NCH 3 ), 7.36 (s, 1H, C-H), 8.27 (d, J=8.8Hz, 2H, Ph-H), 8.38 (d, J=8.8Hz, 2H, Ph-H).

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Abstract

The invention provides a one-pot method for synthesizing N-methylnitrone compounds, comprising the steps of: reducing nitromethane at first with a metal reducing agent, adding aromatic aldehyde directly into a reaction solution for heated reflux to obtain a target product having high yield. The invention uses the nitromethane and the aromatic aldehyde as raw materials, takes organometallic reagents such as zinc, tin and the like as the reducing agent, and employs a one-spot method for the heated reflux to directly synthesize the N-methylnitrone compounds. The method provided by the invention has the characteristics of less synthesis procedures, simple technique, easy operation, easily-available and inexpensive raw materials, mild reaction conditions, low synthesis cost, good product quality and high yield, as well as is an efficient and convenient method for synthesizing the N-methylnitrone compounds.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a method for synthesizing N-methylnitrone compounds, in particular to a method for synthesizing N-methylnitrone compounds in one pot. Background technique [0002] As an important 1,3-dipolar reagent, nitrone compounds play a very important role in the research of 1,3-dipolar cycloaddition reactions. The cycloaddition reaction of nitrones and alkenes can form C-N bonds and C-O bonds. More importantly, the presence of N atoms in nitrones provides a particularly effective and convenient way for the total synthesis of alkaloids and related natural compounds. In particular, N-methylnitrone compounds are the main raw materials and important intermediates for the synthesis of isoxazoline heterocyclic compounds. The resulting isoxazoline heterocyclic compounds are a new class of compounds in the field of pesticides . The structure of N-methylnitrone compounds is as follows: ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/32C07C249/04
Inventor 傅颖王明珠胡雪梅刘彦华肖彩芹张怀远李姣裴菲
Owner NORTHWEST NORMAL UNIVERSITY
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