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Method for synthesizing N-o-nitrophenyl amino acid from o-chloronitrobenzene

A technology of o-nitrophenyl and o-chloronitrobenzene is applied in the field of synthesis of N-o-nitrophenyl amino acids, and can solve problems such as high cost

Inactive Publication Date: 2012-06-27
CHENGDU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, o-iodonitrobenzene is much more expensive than o-chloronitrobenzene

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Add 2 mmol of valine, 3 mmol of o-chloronitrobenzene, 0.2 mmol of cuprous iodide, and 3 mmol of potassium carbonate to the test tube in turn, replace with argon for 3 times, and then add 5 ml of N,N-dimethylformamide , then put the test tube into a 90°C oil bath for heating and stirring reaction, after a certain period of time, cool down, add 15 ml of water to quench the reaction, extract 3 times with 15 ml of ethyl acetate, wash the organic phase twice with water, and then Using the mixed solvent of petroleum ether and ethyl acetate as the eluent, it was separated and purified by silica gel column chromatography to obtain the product N-o-nitrophenylvaline with a yield of 57%.

[0012]

Embodiment 2

[0014] Add 2 mmol leucine, 2.5 mmol o-chloronitrobenzene, 0.3 mmol cuprous iodide, and 3 mmol potassium carbonate to the test tube in turn, replace with nitrogen three times, and then add 5 ml of N,N-dimethylacetamide, Then put the test tube into a 90°C oil bath for heating and stirring to react. After reacting for a certain period of time, cool down, add 15 ml of water to quench the reaction, extract 3 times with 15 ml of ethyl acetate, wash the organic phase twice with water, and then The mixed solvent of petroleum ether and ethyl acetate was used as the eluent, and the product was separated and purified by silica gel column chromatography to obtain the product N-o-nitrophenylleucine with a yield of 56%.

[0015]

Embodiment 3

[0017] Add 2 mmol of phenylalanine, 3 mmol of o-chloronitrobenzene, 0.2 mmol of cuprous iodide, and 3 mmol of potassium carbonate into the test tube in turn, replace with argon for 3 times, and then add 5 ml of N,N-dimethylformaldehyde amide, then put the test tube into a 90°C oil bath for heating and stirring reaction, after a certain period of reaction, cool down, add 15 milliliters of water to quench the reaction, extract 3 times with 15 milliliters of ethyl acetate, wash the organic phase twice with water, Then, the mixed solvent of petroleum ether and ethyl acetate was used as eluent to separate and purify by silica gel column chromatography to obtain the product N-o-nitrophenylphenylalanine with a yield of 57%.

[0018]

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PUM

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Abstract

The invention provides a method for synthesizing an N-o-nitrophenyl amino acid from o-chloronitrobenzene. Under the protection of argon and under the existence of cuprous iodide and potassium carbonate, the o-chloronitrobenzene reacts with amino acid, thereby obtaining the N-o-nitrophenyl amino acid. The method has the advantages of easiness in raw material obtaining, low cost and certain practical value.

Description

technical field [0001] The patent involves the research fields of organic synthesis, organic chemical industry, and drug synthesis, specifically, the synthesis of N-o-nitrophenyl amino acid. [0002] Background technique [0003] N-o-nitrophenyl amino acid can be used to synthesize 3,4-dihydroquinazol-2(1H)-one, which is the intermediate and pharmacophore of the drug. Fu reported a method for the synthesis of N-o-nitrophenyl amino acids by the reaction of o-iodonitrobenzene and amino acids catalyzed by cuprous iodide (SYNLETT, 2007, (12), 1836-1842). However, o-iodonitrobenzene is much more expensive than o-chloronitrobenzene. Contents of the invention [0004] The purpose of the present invention is to provide a method for synthesizing N-o-nitrophenyl amino acid from o-chloronitrobenzene. [0005] The invention is to synthesize 2-aryl quinazolinone compounds by reacting o-chloronitrobenzene and amino acid under an inert atmosphere with 10 (mol)% cuprous iodide as a cat...

Claims

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Application Information

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IPC IPC(8): C07C227/18C07C229/18C07C229/36C07D207/16
Inventor 曾庆乐涂兴钊
Owner CHENGDU UNIVERSITY OF TECHNOLOGY
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