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Preparation method of ortho-amino trifluoroacetophenone and derivatives thereof

A technology of aminotrifluoroacetophenone and trifluoroacetophenone, which is applied in the field of preparation of ortho-aminotrifluoroacetophenone and its derivatives, can solve the difficulty of controlling the nitration site and the degree of nitration , affect the reaction yield, the product is not easy to separate, etc., to achieve good industrial application prospects, improve economic value, and reduce the effect of process steps

Pending Publication Date: 2021-11-16
TAIZHOU ABSOBIOTEC CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the above reaction, first of all, it is difficult to control the nitration site and the degree of nitration, which will be affected by the substituents on the benzene ring, which will affect the yield of the reaction, and the subsequent products are not easy to separate
In addition, the above-mentioned raw materials are not easy to obtain in industry
Therefore, it is difficult to use this pathway in industry

Method used

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  • Preparation method of ortho-amino trifluoroacetophenone and derivatives thereof
  • Preparation method of ortho-amino trifluoroacetophenone and derivatives thereof
  • Preparation method of ortho-amino trifluoroacetophenone and derivatives thereof

Examples

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Embodiment 1～15

[0069] Embodiment 1~15, the preparation method of ortho-aminotrifluoroacetophenone, to comprise the following steps:

[0070] S1. Using compound I as a raw material, under the action of base I, protect the amino group with acid chloride to obtain compound II, and the reaction is shown in formula I;

[0071]

[0072] The specific operation mode of this step reaction is as follows:

[0073] Weigh 5 mol of compound I, dissolve it in 1.5L of ether, and prepare 1L of alkali I aqueous solution with a mass fraction of 40% at the same time, mix the two, cool down to 0°C, and add 1.65mol of acid chloride evenly within 0.5h, and control the reaction during the addition The temperature of the system is lower than 5°C. After adding the acid chloride, raise the temperature of the system to 20°C and continue to stir until the reaction is complete. The reaction time is 2.5 hours. After the reaction was completed, cool down to 0°C and stand still for 1.5 h, then filter, retain the filter ...

Embodiment 16

[0091] Embodiment 16, the preparation method of ortho-aminotrifluoroacetophenone, specifically comprises the following steps:

[0092] S1. Add 30L diethyl ether to the 100L reactor, weigh 5.4kg (30mol) of compound I (2,4-dichloro-3-fluoroaniline), add it to the reactor, and drive n-propanol to cool through the cooling pump to make the reaction The temperature of the solution in the kettle was lowered to 0°C, and then 20L of aqueous sodium hydroxide solution with a mass fraction of 40% was added to it, and while stirring and the condensing pump were kept running, pivaloyl chloride was added dropwise to the reaction kettle. The volume is 3.9L, and the dropping time is 0.5h. During the dropping process, keep monitoring and control the temperature not higher than 5°C. If the temperature rises, speed up the stirring speed and reduce the temperature of n-propanol in the cooling pump.

[0093]After the dropwise addition, stop the cooling pump and return the system in the reactor to r...

Embodiment 1

[0101] Example 17, the preparation method of o-aminotrifluoroacetophenone, differs from Example 1 in that the acid chloride is uniformly added within 20 minutes, the amount of acid chloride is 1.5 mol, and the yield of step S1 is 95.6%.

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Abstract

The invention relates to the field of organic synthesis, in particular to a preparation method of ortho-amino trifluoroacetophenone and derivatives thereof. The preparation of ortho-amino trifluoroacetophenone comprises three steps of amino protection, trifluoroacetylation and deprotection, the overall reaction condition is mild, the yield is high, and the method is suitable for large-scale production. In addition, on the basis of the preparation, substitution is carried out after amino diazotization, the ortho-amino trifluoroacetophenone derivative is further prepared, and the industrial application prospect is good.

Description

technical field [0001] This application relates to the field of organic synthesis, more specifically, it relates to the preparation method of ortho-aminotrifluoroacetophenone and derivatives thereof. Background technique [0002] Trifluoroacetophenone compound and its ortho-amino derivatives are important pharmaceutical intermediates. By setting an amino substitution at the ortho position of the trifluoroacetyl group, different groups can be modified at the ortho position of the trifluoroacetyl group on the benzene ring, thereby achieving different effects. [0003] At present, for the ortho-amino-substituted trifluoroacetophenone and its derivatives, there is no good industrialized production process. In general, trifluoroacetophenone substituted with benzene ring is used as raw material, and then reduced through nitration to obtain trifluoroacetophenone with ortho-amino group. The general reaction formula is as follows: [0004] [0005] In the above reaction, firstly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/22C07C221/00C07C45/65C07C49/80C07C45/63C07C45/64
CPCC07C221/00C07C231/12C07C231/02C07C45/65C07C245/20C07C45/63C07C45/64C07C225/22C07C233/33C07C233/15C07C49/80C07C49/825Y02P20/55
Inventor 张凌霄蔡刚华
Owner TAIZHOU ABSOBIOTEC CO LTD