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Method for N-methylation reaction of nitro-compound

A technology for nitro compounds and aryl nitro compounds is applied in the preparation of amino compounds, the preparation of organic compounds, the preparation of amino hydroxy compounds, etc. Strong Interaction

Active Publication Date: 2019-01-04
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Shi Feng et al. (Chem.Sci., 2014,5,649–655.) from CO 2 / H 2 Starting with CuAlO x The catalyst also realizes the N-methylation reaction of nitro compounds, but the reaction conditions are very harsh, 3.0MPa CO 2 ,7.0MPaH 2 ,170℃,48h

Method used

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  • Method for N-methylation reaction of nitro-compound
  • Method for N-methylation reaction of nitro-compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: take hydrotalcite as the preparation of the Cu-based catalyst of precursor

[0047] Cu(NO 3 ) 2 ·3H 2 O, Al(NO 3 ) 3 9H 2 O is formulated with a molar ratio of 2:1 so that the total concentration of metal ions is 1molL -1 Mixed metal salt solution; NaOH, Na 2 CO 3 Formulated with a molar ratio of 5:1 to prepare a total concentration of Na ions of 1.2molL -1 precipitant solution. Use a dropping funnel to add the metal salt solution and the precipitant solution dropwise into deionized water (the same volume as the metal mixed salt solution), and precipitate under stirring conditions at room temperature. By controlling the drop rate of the metal salt and the precipitant, the system The pH was maintained at 10.0 ± 0.2. After the dropwise addition, it was transferred to an oil bath at 60°C for aging for 15 hours, and the color of the system gradually changed from blue to dark gray. After aging, filter while hot, then wash and filter with deionized wa...

Embodiment 2

[0050] Embodiment 2: Cu-based catalysts catalyze the N-methylation reaction of nitro compounds

[0051] Add 6mg of the Cu catalyst prepared in Example 1 to a thick-walled glass reaction tube, then add 0.25mmol p-nitrotoluene, 150mg paraformaldehyde, 0.5mmol NaCO 3 and 3 mL of solvent H 2 O / DMSO=1:1, the reaction tube was placed in an oil bath with stirring at 130°C for 15 hours, cooled to room temperature, and analyzed by gas chromatography. The results showed that the conversion rate of p-nitrotoluene was 100%, and the selectivity of the product p-methyl N,N-dimethylaniline was 100%.

Embodiment 3 to 10

[0053] Same as Example 2 operation steps, change the kind of aromatic nitro compound (i.e. substrate), in the presence of the Cu-based catalyst prepared in Example 1, complete the N-methylation reaction of other aromatic nitro compounds, each The yields of substrates to generate corresponding methylated products are shown in Table 1:

[0054] Table 1

[0055]

[0056] As can be seen from the results of Examples 1 to 10, the method for the direct N-methylation reaction of nitro compounds according to the present invention can effectively convert various nitro compound substrates into N-methyl products, and the method according to the present invention is cost-effective and beneficial to large-scale industrial production.

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Abstract

The invention discloses a method for direct N-methylation reaction by taking a nitro-compound as a raw material. The method adopts a Cu-based catalyst and polyformaldehyde and can realize the direct N-methylation reaction of the nitro-compound under mild conditions.

Description

technical field [0001] The invention belongs to the field of fine chemical industry, and relates to a method for direct N-methylation reaction using nitro compounds as raw materials. The method adopts Cu-based catalyst and polyoxymethylene to realize direct N-methylation of nitro compounds under mild conditions. methylation reaction. Background technique [0002] Methylation reactions are of great significance in organic synthesis and biological processes, and their products play an important role in the fields of dyes, pharmaceutical synthesis, agrochemicals and fine chemicals. The traditional synthetic route of methylation mainly uses aniline and N-methylating reagent as raw materials. Industrially, aniline is mainly produced by catalytic hydrogenation reduction of nitrobenzene, and its total production is as high as 85% of aniline output. Since the raw materials of aromatic nitro compounds are readily available and cheap, the direct synthesis of N-methylaniline and N,N-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/36C07C211/48C07C211/51C07C211/52C07C213/02C07C215/76C07C217/84C07D213/74C07D241/04
CPCC07C209/36C07C213/02C07D213/74C07D241/04C07C211/48C07C211/51C07C211/52C07C215/76C07C217/84
Inventor 杨勇董晓素
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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