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A kind of synthetic method of 2-aminobenzophenone compounds

A technology of aminobenzophenone and aniline compounds, which is applied in the field of synthesis of 2-aminobenzophenone compounds, and achieves the effects of low energy consumption, mild reaction conditions, economy and good regioselectivity

Active Publication Date: 2021-03-02
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been reported in the literature that N-nitroso-2-aminobenzophenone can be prepared by palladium-catalyzed decarboxylation of N-nitrosoaniline and α-oxocarboxylic acid, but the N-nitroso-2-aminobenzophenone used in this method -Nitrosoaniline is pre-prepared by nitrosating aniline with sodium nitrite and a strong acid system. At the same time, strong oxidants such as potassium persulfate and ammonium persulfate are needed to help the catalyst Pd(II) to regenerate

Method used

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  • A kind of synthetic method of 2-aminobenzophenone compounds
  • A kind of synthetic method of 2-aminobenzophenone compounds
  • A kind of synthetic method of 2-aminobenzophenone compounds

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Experimental program
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Effect test

Embodiment 1

[0016]

[0017] Add N-methylaniline (1a, 0.5mmol, 67mg), 1,2-dichloroethane (2mL), tert-butyl nitrite (2a, 1.5mmol, 180μL) and palladium acetate to a 25mL pressure tube in sequence (0.025mmol, 5.6mg) and benzoylformic acid (3a, 1mmol, 150mg), the pressure tube was sealed and placed in a reactor, stirred and reacted at 40°C for 20 hours. Then iron powder (2mmol, 112mg) and ammonium chloride (1.5mmol, 80mg) were directly added to the above reaction system, and reacted at 80°C for 10 hours. After the reaction, saturated sodium chloride solution (5mL) and ethyl acetate were added ester (8mL), then filtered, the filtrate was extracted with ethyl acetate (5mL×2), the organic phases were combined, dried with anhydrous sodium sulfate, the solvent was recovered by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / acetic acid Ethyl ester=30 / 1, v / v), the product 4a was obtained as a yellow solid (71 mg, 67%). The ch...

Embodiment 2

[0019] Add N-methylaniline (1a, 0.5mmol, 67mg), 1,2-dichloroethane (2mL), tert-butyl nitrite (2a, 1.5mmol, 180μL) and palladium acetate to a 25mL pressure tube in sequence (0.025mmol, 5.6mg) and benzoylformic acid (3a, 1mmol, 150mg), the pressure tube was sealed and placed in a reactor, stirred and reacted at 30°C for 20 hours. Then iron powder (2mmol, 112mg) and ammonium chloride (1.5mmol, 80mg) were directly added to the above reaction system, and reacted at 80°C for 10 hours. After the reaction, saturated sodium chloride solution (5mL) and ethyl acetate were added ester (8mL), then filtered, the filtrate was extracted with ethyl acetate (5mL×2), the organic phases were combined, dried with anhydrous sodium sulfate, the solvent was recovered by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / acetic acid Ethyl ester=30 / 1, v / v), the product 4a was obtained as a yellow solid (61 mg, 58%).

Embodiment 3

[0021] Add N-methylaniline (1a, 0.5mmol, 67mg), 1,2-dichloroethane (2mL), tert-butyl nitrite (2a, 1.5mmol, 180μL) and palladium acetate to a 25mL pressure tube in sequence (0.025mmol, 5.6mg) and benzoylformic acid (3a, 1mmol, 150mg), the pressure tube was sealed and placed in a reactor, stirred and reacted at 50°C for 20 hours. Then iron powder (2mmol, 112mg) and ammonium chloride (1.5mmol, 80mg) were directly added to the above reaction system, and reacted at 80°C for 10 hours. After the reaction, saturated sodium chloride solution (5mL) and ethyl acetate were added ester (8mL), then filtered, the filtrate was extracted with ethyl acetate (5mL×2), the organic phases were combined, dried with anhydrous sodium sulfate, the solvent was recovered by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / acetic acid Ethyl ester=30 / 1, v / v), the product 4a was obtained as a yellow solid (69 mg, 65%).

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Abstract

The invention discloses a synthesis method of 2-aminobenzophenone compounds, belonging to the technical field of organic synthesis. The main points of the technical scheme of the present invention are: using aniline compounds as raw materials, tert-butyl nitrite as nitrosation reagent and oxidant, and α-oxocarboxylic acid compounds as acylating reagents, using Pd(OAc) 2 In situ generated in the catalytic reaction system N ‑C in the nitrosoaniline molecule (sp 2 )-H bond activated acylation reaction, efficient synthesis N ‑Nitroso‑2‑aminobenzophenones, the reducing agent Fe / NH 4 The Cl mixed system is directly added to the above reaction system, which can realize the convenient one-pot synthesis of 2-aminobenzophenone compounds, and the whole process does not require any steps of separation and purification of intermediates. Compared with the methods in the literature, the method of the invention has the advantages of simple starting materials, mild conditions, high efficiency, economy and good regioselectivity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 2-aminobenzophenone compounds. Background technique [0002] 2-Aminobenzophenone compounds not only widely exist in nature, but also are commonly used intermediates in the synthesis of fine chemicals. Therefore, the development of effective synthetic methods for such compounds has always been a research hotspot in organic chemistry and medicinal chemistry. At present, the commonly used synthesis methods mainly include: using the Friedel-Crafts acylation reaction of aromatic hydrocarbons to generate 2-nitrobenzophenone, and then reducing the nitro group; using 2-aminoaromatic aldehydes to react with arylmagnesium bromide Generation of 2-aminobenzhydryl alcohols followed by oxidation; insertion of in situ generated arynes into arylamide molecules, and more. Although these methods are generally more reliable, some methods still have limi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C225/22C07C221/00C07D333/22C07D215/14
CPCC07C221/00C07C225/22C07D215/14C07D333/22
Inventor 王倩倩刘宇飞李娜闫慧娟上官璟芳
Owner XINXIANG MEDICAL UNIV
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