Aromatic-ring C-H bond direct-amination reaction method of aromatic amides

An aryl reaction technology, applied in the field of preparation of aromatic amide compounds, can solve problems such as difficulty, high cost, harsh synthesis conditions, etc.

Active Publication Date: 2017-11-28
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, there are defects such as the need to add expensive metal oxidants such as Ag and react at higher temperatures, making its large-scale preparation difficult.
[0004] To sum up, aromatic amines have important and wide applicability. In the existing synthetic methods, some synthetic conditions are harsh and large-scale preparation is difficult, and some conditions are simple but expensive.

Method used

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  • Aromatic-ring C-H bond direct-amination reaction method of aromatic amides
  • Aromatic-ring C-H bond direct-amination reaction method of aromatic amides
  • Aromatic-ring C-H bond direct-amination reaction method of aromatic amides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the preparation of 2-morpholine-8-aminoquinoline benzoyl

[0052]

[0053] 0.248 g (1.0 mmol) 8-aminoquinoline benzoyl, 0.26 mL (3.0 mmol) morpholine, 0.1 g (0.5 mmol) Cu(OAc) were added sequentially to the 50 mL reaction tube 2 ·H 2 O, 0.276 grams (2.0 mmol) of potassium carbonate, 5 mL of DMF; the reaction was carried out at 70° C. for 3 hours, after the reaction was completed, it was cooled to room temperature, 30 ml of water was added, and then 0.186 grams (0.5 mmol) of EDTA was added and stirred for 30 minutes. Extract the reaction solution with dichloromethane, combine the organic phases and add a desiccant, filter to remove the desiccant, concentrate the organic phase, and use column chromatography to separate and purify the mixture in the reaction solution to obtain the target product 2-morpholine-8 -Aminoquinoline benzoyl 0.300 g (90% yield).

Embodiment 2

[0054] Embodiment 2: Preparation of 2-morpholine-4-methoxy-8-aminoquinoline benzoyl

[0055]

[0056] According to the method and steps described in Example 1, the difference is that 8-aminoquinoline benzoyl is changed to 4-methoxy-8-aminoquinoline benzoyl. Finally, 0.290 g of the target product was obtained (yield 80%).

Embodiment 3

[0057] Embodiment 3: Preparation of 2-morpholine-4-methyl-8-aminoquinoline benzoyl

[0058]

[0059] According to the method and steps described in Example 1, the difference is that 8-aminoquinoline benzoyl is changed to 4-methyl-8-aminoquinoline benzoyl. Finally, 0.288 g of the target product was obtained (yield 83%).

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Abstract

The invention relates to preparation methods for preparing aromatic amide compounds and particularly relates to an aromatic-ring C-H bond direct-amination reaction method of aromatic amides. The method provided by the invention has the characteristics of simplicity, convenience, high efficiency and the like and easily achieves the large-scale preparation of a compound represented by a formula 3 shown in the description. According to the method provided by the invention, a compound represented by a formula 1 shown in the description and a compound represented by a formula 2 shown in the description serve as raw materials, cheap divalent copper serves as a catalyst, oxygen in air serves as an oxidant, and an aromatic-ring C-H bond direct-amination reaction of the aromatic amides is achieved in a high-yield manner. According to the method provided by the invention, the defects of the general preparation of aromatic amides that a reaction substrate is required to be functionalized, a process is relatively tedious and the like are overcome, and the defects of high cost and difficulty in large-scale preparation caused by the additional adding of expensive oxidants such as Ag are also avoided. The method has the characteristics of simplicity, moderateness, relatively good functional group compatibility and the like and has a very good application value.

Description

technical field [0001] The invention relates to a preparation method for preparing aromatic amide compounds, in particular to a method for direct amination reaction of C-H bond of aromatic amide aromatic ring. Background technique [0002] Aromatic amine compounds are a class of organic molecular building blocks with wide applications, and most of their derivatives are organic or polymer functional materials with photoelectric properties. At present, the formation of C-N bonds is mainly through the following methods: 1) amination reaction of metal aryl compounds and nitrogen oxides; 2) metal-catalyzed amination reaction of functionalized aromatic halides and amines; Amination of degrouped amines. These three methods all need to functionalize the reaction substrate, the process is relatively cumbersome, and there are certain limitations in large-scale application. [0003] Aromatic compounds and amines The preparation of aromatic amines under the condition of adding an oxid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/04C07D215/40C07D401/12
CPCB01J27/232B01J31/04B01J35/0006C07D215/40C07D401/12
Inventor 樊新衡陈勇杰杨联明
Owner INST OF CHEM CHINESE ACAD OF SCI
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