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1-phenyl-2-nitroethanol and preparation method of derivatives thereof

A technology of nitroethanol and derivatives, which is applied in the field of preparation of 1-phenyl-2-nitroethanol and its derivatives, can solve the problems of unsuitable purification of products, unsatisfactory catalytic effect, low yield, etc. Low cost, good practicability and easy operation

Inactive Publication Date: 2015-12-02
NANJING UNIV OF INFORMATION SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the process of using these catalysts, we found that the ubiquitous problems of unsatisfactory catalytic effect, low yield, and unsuitable purification of products

Method used

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  • 1-phenyl-2-nitroethanol and preparation method of derivatives thereof
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  • 1-phenyl-2-nitroethanol and preparation method of derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of 1-(2,4-dichloro)phenyl-2-nitroethanol

[0037] Add 15mL t-BuONa / t-BuOH solution (containing t-BuONa2mmol) and 15mLTHF into a 100mL flask, add 10.8mL (0.2mol) nitromethane under stirring, after stirring for a while, add 3.5g (20mmol) 2,4 -Dichlorobenzaldehyde, stirred at room temperature for 5h. After TLC (thin layer chromatography) monitored the completion of the reaction, 30 mL of saturated ammonium chloride solution and 40 mL of ethyl acetate were added and stirred for 10 minutes. After liquid separation, extract the aqueous phase with 30mL*2 ethyl acetate, combine the organic phases, wash twice with 30mL saturated sodium sulfate solution, dry over anhydrous magnesium sulfate, filter, and evaporate the solvent to obtain a nearly colorless oily substance, which is kept at room temperature After 4 hours, the product crystallized and was vacuum-dried at room temperature to obtain 4.2 g of a yellowish powdery solid with a yield of 90%. The m.p. (melting po...

Embodiment 2

[0039] Preparation of 1-phenyl-2-nitroethanol

[0040] 2.1g (20mmol) of benzaldehyde was used instead of 3.5g (20mmol) of 2,4-dichlorobenzaldehyde to react with nitromethane. The synthesis method was the same as in Example 1. The product was an oily substance with a yield of 70%. 1 HNMR (500MHz, CDCl 3 ) analysis result is (see Figure 4 ): δ7.41–7.35(m,5H,Ar-H),5.45(dd, J =10,3Hz,1H,CH-O),4.60(dd, J =13.5Hz,10Hz,1H,-CH 2 -),4.51(dd, J =13.5Hz,3Hz,1H,-CH 2 -), 2.73 (bs, 1H, -OH). The obtained oil was proved to be 1-phenyl-2-nitroethanol.

Embodiment 3

[0042] Preparation of 1-(3-nitro)phenyl-2-nitroethanol

[0043] Add 0.03 g of t-BuOK (2.7 mmol), 5 mL of t-BuOH / THF, and 1.5 mL (28 mmol) of nitromethane into a 100 mL flask, and stir well. Dissolve 0.42g (2.8mmol) of m-nitrobenzaldehyde in 1.5mL of THF, add dropwise into a one-necked bottle, and react under normal temperature and pressure. TLC tracking detection, after the reaction is complete, add 20mL distilled water and 30mL EtOAc (ethyl acetate) to the system, stir and separate the liquid, the aqueous phase is extracted twice with 20mL EtOAc, after combining the organic phase, the organic phase is washed twice with 30mL saturated NaCl, no Water MgSO 4After drying, the solvent was evaporated to give 0.95 g of a pale yellow oil. Recrystallization and purification with PE gave 0.51 g of light yellow solid. Yield 86%. Pale yellow solid m.p. (melting point) is 75-76 oC . 1 HNMR (500MHz, CDCl 3 ) analysis result is (see Figure 5 ): δ8.32(s,1H,Ar-H),8.23(d,1H, J =14Hz,...

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Abstract

The invention discloses a 1-phenyl-2-nitroethanol and a preparation method of derivatives thereof, and the method employs potassium tert-butoxide or sodium tert-butoxide as a catalyst for catalysis of various benzaldehyde derivatives and nitromethane or nitroethane for preparing 1-phenyl-2-nitroethanol and derivatives thereof. The preparation of the invention has the advantages of good catalyst effect, high synthesis reaction conversion rate, high yield which is 50-90%, low cost of crystallization or extraction method for separating, simple operation, non-pollution due to inorganic base catalysis, and good practicality.

Description

technical field [0001] The invention relates to the technical field, in particular to a preparation method of 1-phenyl-2-nitroethanol and derivatives thereof. Background technique [0002] β-aminoalcohol drugs are common natural products and marketed drugs, compounds with aryl β-aminoethanol are a kind of adrenergic receptor agonist drugs, such as salmeterol, salbutamol all have 1-phenyl-2 -aminoethanol structure, used to treat cardiovascular disease and respiratory disease respectively, and β-aminoalcohol can be obtained by reduction of β-nitroalcohol, such as Zhou Yu et al. (Zhou Yu, Liu Juntao, Lu Yixiang, Jia Xian, Li Xingshu. Chinese Journal of Medicinal Chemistry Vol. 19. 2009, Vol.19, No2, 123-126) has prepared salmeterol by this method. [0003] [0004] The preparation of β-nitroalcohol is mainly done through the Henry reaction, and the catalysts currently used in the Henry reaction are mainly divided into three types: inorganic bases, organic bases, and metal-o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/26C07C205/19C07C205/16C07C205/32
Inventor 焦岩张明道陈敏东章翔宇郑江李守光张海英秦芳莲
Owner NANJING UNIV OF INFORMATION SCI & TECH
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