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Synthesis method of 5- hydroxide radical-1-indenone

A synthetic method, the technology of indanone, applied in a new synthetic field, can solve the problems of difficult post-processing, harsh reaction conditions, difficult to obtain raw materials, etc., and achieve the effects of easy operation, rapid preparation, and easy scale-up

Active Publication Date: 2009-11-25
SHANGHAI SYNTHEALL PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves the technical problems such as harsh reaction conditions, difficult post-processing, and difficult to obtain raw materials in the current synthesis method.

Method used

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  • Synthesis method of 5- hydroxide radical-1-indenone
  • Synthesis method of 5- hydroxide radical-1-indenone
  • Synthesis method of 5- hydroxide radical-1-indenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1. Synthesis of phenyl 3-chloropropionate

[0021]

[0022] Phenol (9.4g, 100mmol) was dissolved in 3-chloropropionyl chloride (15g, 120mmol), and the reaction mixture was stirred at 100°C for 12h under nitrogen protection, and detected by TLC until the phenol reaction was complete. The reactant was cooled to room temperature, poured into 120 mL of ice water, extracted with ethyl acetate (120 mL×3), combined the organic phases, washed with 1M NaOH, water and saturated brine, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and reduced Concentrate under reduced pressure to obtain phenyl 3-chloropropionate (16.6g, yield 90%) 1 H NMR (CDCl 3 ): 3.03(t, 2H), 3.85(t, 2H), 7.09-7.12(m, 2H), 7.22-7.26(m, 1H), 7.36-7.40(m, 2H).

[0023] 2. Synthesis of 5-hydroxy-1-indanone

[0024]

[0025] Phenyl 3-chloropropionate (1.85g, 10mmol) was dissolved in trifluoromethanesulfonic acid (4.42mL, 50mmol), and the reaction mixture was placed in an oil bath w...

Embodiment 2

[0028] Synthesis of 5-Hydroxy-1-indanone

[0029]

[0030] Phenyl 3-chloropropionate (1.85g, 10mmol) was dissolved in trifluoromethanesulfonic acid (8.84mL, 100mmol), and the reaction mixture was placed in an oil bath whose temperature had reached 170°C under nitrogen protection and stirred for 2h. The reactant was cooled to room temperature, poured into 20 mL of ice water, extracted with ethyl acetate (20 mL×3), combined the organic phases, washed with saturated sodium bicarbonate, water and saturated brine, dried over anhydrous sodium sulfate, and filtered to remove the desiccant. Concentration under reduced pressure gave 5-hydroxy-1-indanone (710 mg, yield 48%) HPLC (method: 0-60 / 6minute): Rt = 3.03.

Embodiment 3

[0032] Synthesis of 5-Hydroxy-1-indanone

[0033]

[0034] Phenyl 3-chloropropionate (1.85g, 10mmol) was dissolved in trifluoromethanesulfonic acid (17.68mL, 200mmol), and the reaction mixture was placed in an oil bath whose temperature had reached 170°C under nitrogen protection and stirred for 2h. The reactant was cooled to room temperature, poured into 20 mL of ice water, extracted with ethyl acetate (20 mL×3), combined the organic phases, washed with saturated sodium bicarbonate, water and saturated brine, dried over anhydrous sodium sulfate, and filtered to remove the desiccant. Concentration under reduced pressure gave 5-hydroxy-1-indanone (740 mg, yield 50%) HPLC (method: 0-60 / 6minute): Rt=3.03

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Abstract

The invention relates to a new synthesis method of 5- hydroxide radical-1-indenone, which mainly solves the technical problems that reaction conditions are demanding, post-processing is difficult and raw materials are not available of the existing synthesis method. The invention utilizes phenol to be reacted with 3-chlorpromazine chloride to obtain corresponding 3- chloride acid ester of phenol, closing ring to obtain the 5- hydroxide radical-1-indenone under the action of trifluoroacetic acid. The reaction formula is shown as follow. The obtained 5- hydroxide radical-1-indenone is used for medicinal chemistry and organic synthesis.

Description

Technical field: [0001] The present invention relates to a new synthetic method of 5-hydroxyl-1-indanone. Background technique: [0002] 5-Hydroxy-1-indanone and related derivatives are widely used in medicinal chemistry and organic synthesis. The synthesis of this type of compound mainly contains the following three methods to synthesize 5 hydroxy-1-indanone at present: [0003] Method A is to take m-hydroxyphenylacetic acid as raw material, and obtain corresponding product (Hartmann, Rolf W.; Bayer, Herbert; Gruen, Gertrud; J.Med.Chem.1994,1275 -1281). The raw materials of this method are not easy to get, and more importantly, it is not easy to operate and post-process. After the reaction is often completed, the reaction bottle will be smashed to handle the reaction. [0004] The route of literature synthetic method A: [0005] [0006] Method B is to use 5-amino-1-indanone as a raw material, and convert the corresponding amino group into a hydroxyl group by Sanderm...

Claims

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Application Information

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IPC IPC(8): C07C49/733C07C45/67C07C45/51
Inventor 陈秀芝王河清陈林李金鹏勝康弘马汝建陈曙辉
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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