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Method for preparing 2,3-dihydro-1-indanone and derivative thereof

A derivative, indanone technology, applied in the field of preparation 2, can solve the problems of easy fire, large amount, easy to block the pipeline of the reactor, and achieve the effects of low equipment occupancy rate, reduced pollution, and reduced sublimation

Active Publication Date: 2013-04-03
JIANGXI ALPHA HI TECH PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Third, a large amount of petroleum ether is required to purify the intermediate in the first step, which is easy to cause a fire
Fifth, the second step reaction needs to be heated and melted at 180°C, and there is a large amount of AlCl 3 Sublimation can easily clog the reactor pipes

Method used

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  • Method for preparing 2,3-dihydro-1-indanone and derivative thereof
  • Method for preparing 2,3-dihydro-1-indanone and derivative thereof
  • Method for preparing 2,3-dihydro-1-indanone and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 15

[0028] The preparation of embodiment 1.5-chloro-2,3-dihydro-1-indanone

[0029]

[0030] Add chlorobenzene (200g, 1.78mol), aluminum chloride (670g, 5mol), NaCl (110g, 1.88mol) in a 1-liter three-necked flask, stir, and add dropwise 3-chloropropionyl chloride ( 237g, 1.87mol), the mol ratio of chlorobenzene and 3-chloropropionyl chloride is 1: 1.1, and the mol ratio between chlorobenzene, aluminum trichloride and NaCl is 1: 2.8: 1.1, and the dropping temperature is room temperature, in Stir at 45-65°C for 1 hour, raise the temperature to 150-165°C and react for 1 hour, cool to 80-100°C, pour into 2kg of ice water hydrochloric acid, filter with suction to obtain 335g of crude product, and obtain 219.5g of solid after recrystallization. The yield is 74% (purity > 98%), and the melting point is 97-98°C.

[0031] HNMR (ppm, CDCl 3) 7.68-7.71 (m, 1H), 7.45-7.49 (m, 1H), 7.36-7.38 (m, 1H), 3.13-3.16 (t, 2H), 2.71-2.74 (t, 2H).

Embodiment 2

[0032] The preparation of embodiment 2.5-bromo-2,3-dihydro-1-indanone

[0033]

[0034] Add bromobenzene (100g, 0.64mol), aluminum trichloride (212.5g, 1.6mol), NaCl (37g, 0.64mol) into a 1-liter three-necked flask, stir, and add 3-chloropropane dropwise at 20-30°C Acyl chloride (83g, 0.65mol), the molar ratio of bromobenzene and 3-chloropropionyl chloride is 1:1, the molar ratio between bromobenzene, aluminum trichloride and NaCl is 1:2.5:1, at 50~70℃ Stir for 30 minutes at 160-165° C. for 1 hour, cool to 70-80° C., pour into 1 kg of ice-water hydrochloric acid, and suction-filter to obtain 107 g of crude product. After recrystallization, 85 g of solid is obtained, with a yield of 63% (purity> 98%), melting point 127 ~ 128 ℃.

[0035] HNMR (ppm, CDCl 3 ) 7.59-7.64 (m, 2H), 7.48-7.51 (m, 1H), 3.09-3.12 (t, 2H), 2.66-2.69 (t, 2H).

Embodiment 3

[0036] The preparation of embodiment 3.5-fluoro-2,3-dihydro-1-indanone

[0037]

[0038] Add fluorobenzene (96g, 1mol), aluminum chloride (333g, 2.5mol), NaCl (65g, 1.1mol) in a 1-liter three-necked flask, stir, and add dropwise 3-chloropropionyl chloride ( 133g, 1.05mol), the molar ratio of fluorobenzene and 3-chloropropionyl chloride is 1: 1.1, the molar ratio between fluorobenzene, aluminum trichloride and NaCl is 1: 2.5: 1.1, stirring at 65~70°C 2 hours, stirred at 165-175°C for 3 hours, cooled to 75-80°C, poured into 1kg of ice-water hydrochloric acid, filtered with suction to obtain 134g of crude product, and obtained 84g of solid after recrystallization, with a yield of 56% (purity>98%) ), with a melting point of 38-39°C.

[0039] HNMR (ppm, CDCl 3 ) 7.75-7.78 (m, 1H), 7.57-7.59 (m, 1H), 7.42-7.45 (m, 1H), 3.17-3.20 (t, 2H), 2.85-2.87 (t, 2H).

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Abstract

The invention relates to a synthetic method of indanone substances, and particularly relates to a method for preparing 2,3-dihydro-1-indanone and a derivative thereof. The method comprises the following steps of: mixing benzene substituendum of which the structure is shown in a formula (I) with AlCl3 / NaCl, dropwise adding 3-chloropropionylchloride under agitation, and reacting to prepare the 2,3-dihydro-1-indanone and the derivative thereof in one step, wherein R1 and R2 are H atoms, halogen atoms, C1-C10 alkyl, methoxyl, ethyoxyl or amino; dropwise adding 3-chloropropionylchloride at 0-40 DEG C, wherein the control temperature is 0-60 DEG C and the retention time is 0.5-3hours; carrying out Fuke acylation reaction, heating to 150-200 DEG C to keep for 0.5-4hours; and carrying out cyclization reaction, and hydrolyzing cyclization reaction products, wherein the hydrolysis temperature is 50-100 DEG C. Two steps of reaction are merged into a one-pot method. Thus, purifying, drying and packaging of a midbody are reduced; the allergy possibility is avoided; the usage amount of a catalyst is reduced; and the production cost is reduced, and the environmental pollution is also reduced.

Description

technical field [0001] The invention relates to a method for synthesizing indanones, in particular, the invention relates to a method for preparing 2,3-dihydro-1-indanone and derivatives thereof. Background technique [0002] 2,3-Dihydro-1-indanone is an important chemical raw material with simple structure and wide application, and is an important intermediate for the synthesis of various medicines and pesticides. Various indanone structures with different structures widely exist in natural products isolated from plants and marine organisms. Many compounds containing indanone structure exhibit various physiological and pharmacological activities, including antitumor activity and inhibition of acetylcholinesterase (acetylcholinesterase) activity. For example, the famous Donepezil (Aricept) has a good curative effect on Alzheimer's disease. Some indanones have been produced industrially, such as 5-fluoro-2,3-dihydro-1-indanone, 5-bromo-2,3-dihydro-1-indanone, 5-chloro-2,3-bi...

Claims

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Application Information

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IPC IPC(8): C07C45/46C07C49/697C07C49/67C07C49/755C07B41/06
Inventor 黄云生繆志毅
Owner JIANGXI ALPHA HI TECH PHARMA
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