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Technique of preparing m-nitrobenzene acetylene

A technology for the preparation of nitrophenylacetylene, which is applied in the field of preparation of m-nitrophenylacetylene, can solve the problems of long-time heating, long reaction time, instability of m-nitroiodobenzene, etc., and achieves mild reaction conditions and short reaction time. Short, easy post-processing effects

Inactive Publication Date: 2008-09-24
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The operation steps of this invention are not very complicated, but the reaction time is relatively long, a large amount of chemical substances such as strong corrosive acid and alkali are used, and long-term heating is required
U.S. Patent U.S.Pat.Appl.5902902 utilizes m-aminobromobenzene and 2-methyl-3-butyn-2-alcohol to react under the catalysis of palladium chloride, cuprous chloride, etc. to form 4-(3-amino Phenyl)-2-methyl-3-butyn-2-alcohol, then treated with sodium hydroxide to obtain the target compound, requires a noble metal salt as a catalyst, and the price of 2-methyl-3-butyn-2-alcohol is relatively high And unstable, no doubt the cost of synthesis will increase
U.S. Patent U.S.Pat.Appl.6127583 utilizes m-nitroacetophenone and chloride 1,3-dimethyl-2 fluoroimidazolinium to react m-nitrophenylacetylene, chloride 1,3-dimethyl- The preparation of 2 fluoroimidazolinium is cumbersome and the product yield is low
The world patent WO2007067506 reports the use of m-nitroiodobenzene and trimethylethynyl silicon in the presence of diisopropylamine, cuprous iodide and dichlorotriphenylphosphopalladium to form 3-nitrophenylethynyl Trimethylsilyl, then treated with tetrabutylammonium fluoride to obtain m-nitrophenylacetylene, the reagents used are relatively expensive, and m-nitroiodobenzene is unstable, post-treatment involves column chromatography separation and purification, and the operation is more cumbersome

Method used

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  • Technique of preparing m-nitrobenzene acetylene
  • Technique of preparing m-nitrobenzene acetylene
  • Technique of preparing m-nitrobenzene acetylene

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Dissolve 6 g of m-nitrobenzaldehyde in 80 ml of anhydrous methanol, blow nitrogen, add 11 g of anhydrous potassium carbonate and 10.6 g of Bestmann-Ohira reagent, stir and react at room temperature for 24 hours under nitrogen atmosphere, filter, collect the filtrate, and evaporate under reduced pressure Organic solvent, the residue was dissolved in 20ml of dichloromethane, the dichloromethane solution was washed successively with 240ml of 5% sodium bicarbonate and saturated brine, the organic layer was separated, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a light yellow Nitrophenylacetylene solid 5.5g, mp25-26°C, yield 93.5%.

Embodiment 2

[0019] Dissolve 6 g of m-nitrobenzaldehyde in 100 ml of anhydrous methanol, pass through nitrogen, add 12.8 g of anhydrous potassium carbonate and 12.5 g of Bestmann-Ohira reagent, stir and react at room temperature for 24 h under nitrogen atmosphere, filter, collect the filtrate, and evaporate under reduced pressure Remove the organic solvent, dissolve the residue with 30ml of ethyl acetate, wash the ethyl acetate solution with 240ml of 5% sodium bicarbonate and saturated brine successively, separate the organic layer, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure to obtain light yellow m-nitrophenylacetylene solid 5.6g, mp25-26.5°C, yield 95.2%.

Embodiment 3

[0021] Dissolve 5 g of m-nitrobenzaldehyde in 80 ml of anhydrous methanol, pass through nitrogen, add 10 g of anhydrous potassium carbonate and 8 g of Bestmann-Ohira reagent, stir and react at room temperature under nitrogen atmosphere for 24 h, filter, collect the filtrate, and evaporate organic matter under reduced pressure. Solvent, the residue was dissolved in 30ml of chloroform, the chloroform solution was washed successively with 200ml of 5% sodium bicarbonate and saturated brine, the organic layer was separated, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a light yellow m-nitrophenylacetylene solid 4.3g, mp25-26.5°C, yield 88.4%.

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Abstract

The present invention relates to a preparation process of m-nitrobenzene acetylene. The preparation process comprises the following steps: m-nitrobenzaldehyde and Bestmann-Ohira agent react with carbonate or alkoxide, so as to prepare the m-nitrobenzene acetylene. The preparation process starts from the m-nitrobenzaldehyde to prepare the target product through one-step operation; the reaction time is short; the reaction conditions are mild; the post treatment is easy; no column chromatography is required; and the preparation process is simple, economic and practical.

Description

technical field [0001] The invention relates to a preparation process of m-nitrophenylacetylene. Background technique [0002] m-Nitrophenylacetylene is the precursor of the indispensable intermediate m-aminophenylacetylene in the synthesis of the compound "erolotinib". Erlotinib is an epidermal growth factor receptor tyrosine kinase inhibitor (Tyrosine Kinase Inhabitor). Erlotinib acts by inhibiting the intracellular phosphorylation of epidermal growth factor receptor tyrosine kinase. Epidermal growth factor receptor (EGFR) is a member of the ErbB family and has tyrosine kinase activity , is an important transmembrane receptor. After EGFR is activated by ligands, intracellular signal transduction is initiated, and through the cascade reaction of adapter proteins and enzymes in the cytoplasm, it regulates the transcription of transcription factor-activated genes and guides cell migration, adhesion, proliferation, differentiation, and apoptosis. EGFR signal transduction is ...

Claims

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Application Information

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IPC IPC(8): C07C205/06C07C201/12
Inventor 冯润良宋智梅
Owner UNIV OF JINAN
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