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Synthesis method of 2-(4-nitrophenyl) butyric acid

A synthetic method, nitrophenyl technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as the impact of environmental impact assessment, and achieve the effect of convenient operation, less pollution, and simple steps

Pending Publication Date: 2022-05-20
HANGZHOU ZHONGMEI HUADONG PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, affected by the environmental impact, the production involving nitration reaction is strictly controlled. In order to reduce the risk, it is necessary to develop a new preparation method of 2-(4-nitrophenyl)butyric acid

Method used

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  • Synthesis method of 2-(4-nitrophenyl) butyric acid
  • Synthesis method of 2-(4-nitrophenyl) butyric acid
  • Synthesis method of 2-(4-nitrophenyl) butyric acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]

[0022]In the reaction bottle, SM2 (1.41g, 10.00mmol) was dissolved in DMF, cooled to 0 °C, NaH (0.28g, 12.00mmol) was added under the ice bath, stirred for half an hour and then dripped diethyl malonate (2.83g, 15.00mmol), the ice bath was removed, and the reaction at room temperature was 12h. After the reaction was completed, the reaction solution was poured into water, extracted with ethyl acetate, combined with organic phase, washed with saturated brine, dried anhydrous sodium sulfate, and purified by column chromatography to give a light yellow oily liquid C002.10g, with a yield of 67%.

[0023] 1 H NMR(60MHz,CDCl 3 )δ8.44–8.02(m,2H),7.88–7.48(m,2H),4.53–4.08(m,4H),2.39(q,J＝7.4Hz,2H),1.06(dt,J＝22.6,7.3Hz,9H).

[0024] HRMS(ESI):found 310.1290[M+H] +

Embodiment 2

[0026]

[0027] Add SM2 (1.41 g, 10.00 mmol) and K to the reaction flask 2 CO 3 (4.14g, 30.00mmol), dissolved in DMF, stirred and dripped with diethyl malonate (2.83g, 15.00mmol), room temperature reaction 12h. After the reaction was completed, the reaction solution was poured into water, extracted with ethyl acetate, combined with the organic phase, washed with saturated salt water, dried anhydrous sodium sulfate, and purified by column chromatography to give a pale yellow oily liquid C00 2.00g, with a yield of 64%.

[0028] 1 H NMR(60MHz,CDCl 3 )δ8.44–8.02(m,2H),7.88–7.48(m,2H),4.53–4.08(m,4H),2.39(q,J＝7.4Hz,2H),1.06(dt,J＝22.6,7.3Hz,9H).

[0029] HRMS(ESI):found 310.1290[M+H] +

Embodiment 3

[0031]

[0032] In the reaction bottle, C00 (0.31g, 1.00mmol), dissolved in acetic acid, stirred and dripped 50% concentrated sulfuric acid (0.6mL, 3.00mmol), 120 °C reaction for 24h. After the reaction, the reaction liquid is dried, add water, NaOH is adjusted to alkaline, dichloromethane extraction, the organic phase is discarded, the aqueous phase is adjusted to pH to acidic with HCl, dichloromethane is extracted, the organic phase is saturated with salt water washed, the anhydrous sodium sulfate is dried, and the pale yellow solid B00 is obtained by spinning drying to obtain a pale yellow solid B00 1.50g, with a yield of 76%.

[0033] 1 H NMR(60MHz,DMSO-d 6 )δ8.48–7.97(m,2H),7.85–7.36(m,2H),3.72(d,J＝7.4Hz,1H),2.28–1.59(m,2H),0.83(t,J＝7.2Hz,3H).

[0034] HRMS(ESI):found 208.0615[M-H] -

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Abstract

The invention discloses a synthesis method of 2-(4-nitrophenyl) butyric acid, which comprises the following steps: in an organic solvent, under the action of an alkaline substance, reacting a compound as shown in a formula I with diethyl malonate to obtain a compound as shown in a formula II; and hydrolyzing the compound as shown in the formula II under an acidic condition to obtain a target product as shown in a formula III. The method provided by the invention has the advantages of simple steps, convenience in operation, no nitration process in reaction, high safety, small pollution and high product yield.

Description

Technical field [0001] The present invention belongs to the field of compound synthesis, specifically relates to a synthesis method of 2- (4-nitrophenyl) butyric acid. Background [0002] Indobufen (indobufen) chemical name 2-[4- (1-oxo2-isoindoleline) phenyl] butyric acid is a racemate mixture developed by Pfizer Corporation of the United States, which can select the circulating platelets, block thrombosis, inhibit the release of platelet factors and exert antiplatelet aggregation, this inhibition is reversible, does not change plasma parameters, does not affect platelet function, and normalizes abnormal platelet function. Compared with similar drugs, indolebufen inhibits platelet factors, and the antiplatelet aggregation effect is 2 to 5 times that of salicylic acid, and there is a shorter bleeding time than that of slight duration. [0003] Gao Xuemin et al. in the "synthesis of anticoagulant indolebufen" (Chinese Journal of Pharmaceutical Industry, 1989, 20 (11)), Zheng Gengx...

Claims

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Application Information

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IPC IPC(8): C07C205/56C07C201/12
CPCC07C201/12C07C205/56
Inventor 靳浩吴沣方丽
Owner HANGZHOU ZHONGMEI HUADONG PHARMA
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