Synthesizing method of 2-amino-4'-fluoro-benzophenone

A technology of benzophenone and synthesis method, which is applied in the fields of chemical instruments and methods, preparation of organic compounds, organic chemistry, etc. It can solve Friedel-Crafts reaction with many side reactions, total yield of only 49%, long reaction steps, etc. problem, to achieve the effect of excellent product quality, simple equipment, and short reaction cycle

Active Publication Date: 2013-05-08
CHAMBROAD CHEM IND RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Among the above three preparation methods, the first method Friedel-Crafts reaction has many side reactions, and the yield only has 44%; the second method has long reaction steps, and the total yield only has 49%; although the third method has a high yield, However, too many reagents are required and the cycle is too long

Method used

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  • Synthesizing method of 2-amino-4'-fluoro-benzophenone

Examples

Experimental program
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Effect test

Embodiment 1

[0021] A kind of synthetic method of 2-amino-4'-fluoro-benzophenone, its concrete steps are:

[0022] (1) Preparation of 2-p-fluorobenzoylbenzamide

[0023] Add 29.42g of phthalimide and 19.61g of fluorobenzene into dichloroethane, add 13.34g of anhydrous aluminum trichloride at room temperature, raise the temperature to 55°C, keep it warm for 4 hours until the reaction is complete, and recover dichloromethane under reduced pressure. Ethane, cool to room temperature, add 110ml of dichloromethane, slowly pour the reaction solution into ice water containing hydrochloric acid under stirring, adjust the pH value to 2, separate liquid, wash with water, recover dichloromethane under reduced pressure, and precipitate a large amount of solid , washed with water and dried to obtain 46.86g of white powdery 2-p-fluorobenzoylbenzamide, with a content of 97.5% and a yield of 96.42%;

[0024] (2) Preparation of 2-amino-4'-fluoro-benzophenone

[0025] Add 24.32g of 2-p-fluorobenzoylbenzami...

Embodiment 2

[0027] A kind of synthetic method of 2-amino-4'-fluoro-benzophenone, its concrete steps are:

[0028] (1) Preparation of 2-p-fluorobenzoylbenzamide

[0029] Add 29.42g of phthalimide and 21.14g of fluorobenzene into dichloroethane, add 18.66g of anhydrous aluminum trichloride at room temperature, raise the temperature to 65°C, keep it warm for 5h until the reaction is complete, and recover dichloromethane under reduced pressure. Ethane, cool to room temperature, add 100ml of dichloromethane, slowly pour the reaction solution into ice water containing hydrochloric acid under stirring, adjust the pH value to 4, separate liquid, wash with water, recover dichloromethane under reduced pressure, and precipitate a large amount of solid , washed with water and dried to obtain 46.12g of white powdery 2-p-fluorobenzoylbenzamide, with a content of 97.7% and a yield of 94.82%;

[0030] (2) Preparation of 2-amino-4'-fluoro-benzophenone

[0031]Add 24.32g of 2-p-fluorobenzoylbenzamide int...

Embodiment 3

[0033] A kind of synthetic method of 2-amino-4'-fluoro-benzophenone, its concrete steps are:

[0034] (1) Preparation of 2-p-fluorobenzoylbenzamide

[0035] Add 29.42g of phthalimide and 20.38g of fluorobenzene into dichloroethane, add 16.00g of anhydrous aluminum trichloride at room temperature, raise the temperature to 60°C, keep it warm for 4.5h until the reaction is complete, and recover di Chloroethane, cooled to room temperature, add 105ml of dichloromethane, slowly pour the reaction solution into ice water filled with hydrochloric acid under stirring, adjust the pH value to 3, separate liquid, wash with water, recover dichloromethane under reduced pressure, and precipitate a large amount of The solid was washed with water and dried to obtain 46.56 g of white powdery 2-p-fluorobenzoylbenzamide, with a content of 98.1% and a yield of 95.73%;

[0036] (2) Preparation of 2-amino-4'-fluoro-benzophenone

[0037] Add 24.32g of 2-p-fluorobenzoylbenzamide into 50ml of water, a...

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Abstract

The invention belongs to the technical field of fine chemicals. The invention relates to a pharmaceutical chemical synthesis technology, and especially relates to a synthesizing method of 2-amino-4'-fluoro-benzophenone. According to the invention, o-phthalimide is adopted as an initial raw material for a first time, and is subjected to a Friedel-Crafts reaction with fluorobenzene, such that 2-p-luorobenzoyl benzamide is obtained; and through Hofmann degradation, 2-amino-4'-fluoro-benzophenone is obtained. The method has the advantages of short reaction period, high conversion rate, and good product quality. The content of produced 2-amino-4'-fluoro-benzophenone is higher than 99%, such that technical requirement by the market for 2-amino-4'-fluoro-benzophenone is satisfied. The operation steps and required devices are simple, and energy consumption is low.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, relates to the synthesis technology of pharmaceutical chemicals, and particularly relates to a synthesis method of 2-amino-4'-fluoro-benzophenone. Background technique [0002] Pitavastatin calcium is an effective anti-cholesterol drug, 2-amino-4'-fluoro-benzophenone is an important intermediate in the synthesis of pitavastatin calcium (E)-3-[2-cyclopropyl-4 -The key raw material of (4-fluoro-phenyl)-3-quinolyl]acrolein, which plays an important role in organic synthesis and has broad market prospects. [0003] At present, the preparation of 2-amino-4'-fluoro-benzophenone has the following methods: 1. Taking isatoic anhydride as raw material, first reacting with thionyl chloride to generate o-chloroformyl isocyanate, and then reacting with isocyanate Fluorobenzene is prepared by Friedel-Crafts reaction and deprotection agent; 2. Using anisole as raw material, first protect the amino group...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/22C07C221/00
Inventor 王朋朋吴文雷栾波马韵升安敬瑞许倩倩曹斌
Owner CHAMBROAD CHEM IND RES INST CO LTD
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