Preparation method of N-cyclopropyl methylaniline compound

A technology of cyclopropylmethylaniline and compounds, which is applied in the field of preparation of N-cyclopropylmethylaniline compounds, can solve the problems of a large amount of solid residue and post-processing difficulties, achieve less impurities, reduce post-processing operations, and simple process Effect

Pending Publication Date: 2022-06-07
JIANGXI UNIVATE NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] Although this method has a high yield, metal zinc powder is used in the reaction process, which will produce a large amount of solid residue, making post-processing difficult.

Method used

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  • Preparation method of N-cyclopropyl methylaniline compound
  • Preparation method of N-cyclopropyl methylaniline compound
  • Preparation method of N-cyclopropyl methylaniline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The present embodiment prepares 3-[(cyclopropylmethyl)amino]-2-fluorobenzoic acid methyl ester, and the reaction formula is as follows:

[0060]

[0061] Into the 500mL autoclave, 40.2g of 3-nitro-2-fluoro-methyl benzoate (0.2mol, 99% purity), 0.2g of 5% platinum carbon catalyst, 7.96g of acetic acid (0.13mol, 99% purity), Cyclopropylcarbaldehyde 16.8g (0.24mol, purity 99%) and methanol 119.4g were hydrogenated to a pressure of 1.0MPa and reacted at 40°C for 12h. After the reaction, filter, wash the filter residue with 20g methanol, combine the filtrates to remove the solvent under reduced pressure, and dry to obtain 43.2g of methyl 3-[(cyclopropylmethyl)amino]-2-fluorobenzoate, content 98.5% (external standard method, the same below), the yield was 95.4% (mass yield, the same below).

[0062] The characterization data is as follows:

[0063] LC / MS [M+1]: m / z=224.

[0064] 1 H NMR (400MHz, CDCl3) data as follows (δ[ppm]): 7.18-7.15 (m, 1H), 7.05-7.01 (m, 1H), 6.8...

Embodiment 2

[0066] The present embodiment prepares 3-[(cyclopropylmethyl)amino]-2-fluorobenzoic acid ethyl ester, and the reaction formula is as follows:

[0067]

[0068] In the 500mL autoclave, 43.0g of 3-nitro-2-fluoro-ethyl benzoate (0.2mol, 99% purity), 0.42g of 5% platinum carbon catalyst, 8.52g of acetic acid (0.14mol, 99% purity), Cyclopropylcarbaldehyde 19.6g (0.28mol, purity 99%) and ethanol 213g were hydrogenated to a pressure of 2.0MPa and reacted at 60°C for 14h. After the reaction, filter, wash the filter residue with 20g ethanol, combine the filtrates to remove the solvent under reduced pressure, and dry to obtain 3-[(cyclopropylmethyl)amino]-2-fluorobenzoic acid ethyl ester 45.1g, content 98.0%, yield was 93.2%.

[0069] Characterization data:

[0070] LC / MS [M+1]: m / z=238.

Embodiment 3

[0072] The present embodiment prepares 3-[(cyclopropylmethyl)amino]-2-fluorobenzoic acid propyl ester, and the reaction formula is as follows:

[0073]

[0074] In the 500mL autoclave, 45.9g of 3-nitro-2-fluoro-propyl benzoate (0.2mol, 99% purity), 0.91g of 5% platinum carbon catalyst, 18.16g of acetic acid (0.30mol, 99% purity), Cyclopropylcarbaldehyde 22.4 g (0.32 mol, purity 99%) and ethyl acetate 136.2 g were hydrogenated to a pressure of 3.0 MPa, and reacted at 100° C. for 16 h. After the reaction was completed, filter, wash the filter residue with 20 g of ethyl acetate, combine the filtrates to remove the solvent under reduced pressure, and dry to obtain 48.5 g of 3-[(cyclopropylmethyl)amino]-2-fluorobenzoic acid propyl ester with a content of 97.5%, The yield was 94.2%.

[0075] Characterization data:

[0076] LC / MS [M+1]: m / z=252.

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Abstract

The invention relates to a preparation method of an N-cyclopropyl methylaniline compound, and the preparation method comprises the following steps: taking a compound as shown in a formula II and cyclopropyl formaldehyde as raw materials, and carrying out hydrogenation reaction under the action of acid and a catalyst to obtain the N-cyclopropyl methylaniline compound as shown in a formula I. The N-cyclopropyl methylaniline compound as shown in a formula I is shown in the description, r is selected from alkoxy, alkylamino or substituted anilino as shown in a formula III. According to the preparation method disclosed by the invention, two-step reaction of nitro reduction and aminoalkylation is carried out by adopting a'one-pot method 'through a catalytic hydrogenation method by utilizing the raw materials of the compound as shown in the formula II and cyclopropyl formaldehyde, so that post-treatment operation is reduced, the process is simple and convenient, the operation is simple, the cost is low, the production is clean, meanwhile, the reaction yield is increased, and the preparation method is suitable for industrial production. According to the preparation method, few impurities are generated, so that the yield of the product is high, the product can obtain relatively high purity through simple post-treatment, and complicated and tedious post-treatment is not needed.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pesticides and insecticides, relates to a preparation method of N-cyclopropylmethylaniline compounds, and in particular relates to a method for preparing N-cyclopropylmethylaniline compounds by adopting a "one-pot method" The method, in particular, relates to a preparation method of N-cyclopropylmethylaniline compounds with low cost, clean production, high yield and simple operation. Background technique [0002] N-Cyclopropylmethylaniline is an important intermediate for the preparation of meta-diamide compounds. For example, in the synthesis of the recently reported meta-diamide insecticide ciprofloxacin (CAS: 2375110-88-4), it is necessary to Such intermediates are used, which are compounds having the general structural formula shown in Formula I: [0003] [0004] wherein R is alkoxy, alkylamino or substituted aniline [0005] The prior art discloses some reports on the preparation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/60C07C227/04C07C237/40C07C231/12C07C237/30
CPCC07C227/04C07C231/12C07C2601/02C07C229/60C07C237/40C07C237/30C07C221/00
Inventor 黄超群朱锦涛吕亮罗亮明张荣刘吉永
Owner JIANGXI UNIVATE NEW MATERIAL CO LTD
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