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Preparation of compound namely [2-(hydroxyl-4-pyridazine methyl)-3,4-dihydronaphthol-1-(2H)-ketone]

A technology of dihydronaphthol and pyridazine methyl is applied in the field of preparation of pyridazine compound 2--3,4-dihydronaphthol-1-one, which can solve the problem of long reaction time, low synthesis efficiency, High cost and other issues, to achieve the effects of low toxicity and volatility, mild synthesis conditions, and short synthesis time

Active Publication Date: 2014-02-05
北京汇康博源医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the catalyst diethylamine is volatile and has acute toxicity, it is not conducive to environmental protection; in addition, the reaction is carried out under refrigerated conditions, and the reaction time is long, the synthesis efficiency is low, and the cost is high, which is not conducive to industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1. Take a 10M reaction tube as a reactor, weigh 7.1 mg of pyrrolidine and dissolve it in 2.0 mL of dichloromethane, then add 15.0 mg of trifluoromethanesulfonic acid, stir at room temperature for 10 minutes, and then add 146 mg 3,4 -Dihydronaphthol-1-(2H)-ketone and 110mg 4-pyridazinecarboxaldehyde, react at room temperature for 22h, then follow the reaction by thin-layer chromatography. After the reaction is completed, direct column chromatography to separate 180mg of white solid product, which is the target product The yield was 71%.

[0016] The melting point of the obtained product is 125 ~126 ℃.

[0017] The NMR data of the obtained product are as follows:

[0018] 1 H NMR (DMSO- d 6 , 400 MHz, TMS): 9.28 (d, 1.6 Hz, 1H), 9.22-9.16 (m, 1H), 7.71-7.66 (m, 1H), 7.40-7.32 (m, 2H), 7.58-7.52 (m, 1H), 7.81 (dd, 7.8 Hz, 1.2 Hz, 1H), 5.80 (d, 4.9 Hz, 1H), 5.60-5.58 (m, 1H), 3.04-2.90 (m, 1H), 2.99-2.84 (m, 2H), 2.08-1.96 (m, 1H), 1.70-1.62 (m, 1H).

[0019] The high re...

Embodiment 2

[0022] Example 2. Take a 50 mL round bottom flask as a reactor, weigh 71 mg of pyrrolidine and dissolve it in 20 mL of dichloromethane, then add 150 mg of fluoromethanesulfonic acid, stir at room temperature for 15 minutes, and then add 0.75 g of 3,4-di Hydronaphthol-1-(2H)-one and 0.60g 4-pyridazinecarboxaldehyde were reacted at room temperature for 24h. The reaction was followed by thin-layer chromatography. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain 0.86g of a white solid product. , The yield is 66%.

[0023] The melting point, nuclear magnetic data, and mass spectrometry data of the product are the same as in Example 1.

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Abstract

The invention provides a preparation method of a compound namely [2-(hydroxyl-4-pyridazine methyl)-3,4-dihydronaphthol-1-(2H)-ketone], belonging to the technical field of fine chemical industry. According to the preparation method, the compound is obtained by taking dichloromethane as a solvent, pyrrolidine as a catalyst and trifluoromethanesulfonic acid as an auxiliary catalyst and enabling 4-pyridazine formaldehyde to react with 3,4-dihydronaphthol-1-(2H)-ketone for 20-24 hours at room temperature according to a mole ratio of 1.0: (0.9-1.0):1.2. The catalyst namely pyrrolidine and the auxiliary catalyst namely trifluoromethanesulfonic acid adopted in the preparation method provided by the invention are small in toxicity and volatility, safe and environment-friendly; the synthetic condition is mild (room temperature), the synthetic time is short (within 4 hours), the reaction efficiency is high, and the cost is low, so that the preparation method is favorable for industrial production.

Description

Technical field [0001] The invention belongs to the technical field of fine chemicals, and relates to a preparation method of pyridazine compound 2-(hydroxy-4-pyridazinemethyl)-3,4-dihydronaphthol-1-(2H)-one. Background technique [0002] Pyridazine compounds are a class of N heterophenyl ring compounds, which have important applications in the field of biomedicine. For example, pyridazinone compounds can be used as inhibitors of phosphodiesterase 10A (PDE10A) for the treatment of schizophrenia, Drug addiction, Parkinson's disease and other diseases. The introduction of different groups into the pyridazine structure can produce pyridazine derivatives with bactericidal activity, which plays an important role in the creation of new and efficient pesticides. The pyridazine compound-2-(hydroxy-4-pyridazinemethyl)-3,4-dihydronaphthol-1-(2H)-one is a typical pyridazine, and its structural formula is as follows: [0003] [0004] Studies have shown that the compound can be used as an in...

Claims

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Application Information

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IPC IPC(8): C07D237/08
CPCC07D237/08
Inventor 唐海峰韩欣蔚周小光
Owner 北京汇康博源医药科技有限公司