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Synthesis method of N-aryl hydroxylamine acid

A technology for the synthesis of aryl hydroxyamic acid and its method, which is applied in the field of synthesis of N-aryl hydroxyamic acid, can solve the problems of harsh operating conditions, difficult handling, and moisture sensitivity of acyl chlorides, and achieve mild operating conditions and simple separation and purification operations Effect

Inactive Publication Date: 2012-10-03
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The first method has the disadvantages that raw materials are easy to decompose, such as acid chlorides are sensitive to moisture in the air, easily absorb water and deteriorate, and are difficult to handle. The operating conditions are harsh, and the other two methods have the disadvantages of low yield and selectivity.

Method used

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  • Synthesis method of N-aryl hydroxylamine acid
  • Synthesis method of N-aryl hydroxylamine acid
  • Synthesis method of N-aryl hydroxylamine acid

Examples

Experimental program
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Effect test

Embodiment 1

[0033]

[0034] The specific process is as follows:

[0035] In a 100mL single-necked flask, add 50mL of dried dichloromethane, and then add 0.465g of aniline and 0.530g of benzaldehyde in sequence, and the molar ratio of aniline and benzaldehyde is 1:1. Stir well at room temperature, react for 6 hours, add 50 mL of saturated saline, and quench the reaction. It was extracted three times with dichloromethane, and 50 mL of dichloromethane was used each time. The organic phases were combined, dried with anhydrous sodium sulfate, and evaporated to dryness of dichloromethane to obtain a solid, namely intermediate A, with a yield of 95%.

[0036] Take 197 mg of intermediate A, add it to 10 mL of dried dichloromethane, stir to dissolve, then place it in an ice-water bath (0°C), add 102 mg of sodium bicarbonate and 258 mg of m-chloroperoxybenzoic acid (m- CPBA), after stirring for half an hour, the temperature of the reaction solution rose to room temperature, and after 12 hours ...

Embodiment 2

[0038]

[0039] The specific process is as follows:

[0040] In a 100mL single-necked flask, add 50mL of dried dichloromethane, and then add 0.465g of aniline and 0.660g of cinnamaldehyde in sequence, and the molar ratio of aniline and cinnamaldehyde is 1:1. Stir well at room temperature, react for 6 hours, add 50 mL of saturated saline, and quench the reaction. It was extracted three times with dichloromethane, and 50 mL of dichloromethane was used each time. The organic phases were combined, dried with anhydrous sodium sulfate, and evaporated to dryness of dichloromethane to obtain a solid, namely intermediate B, with a yield of 98%.

[0041] Take 207 mg of intermediate B, add it to 10 mL of dried dichloromethane, stir to dissolve, then place it in an ice-water bath (0°C), add 102 mg of sodium bicarbonate and 258 mg of m-chloroperoxybenzoic acid (m- CPBA), after stirring for half an hour, the temperature of the reaction solution rose to room temperature, and after 12 ho...

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Abstract

The invention discloses a synthesis method of N-aryl hydroxylamine acid, wherein the synthesis method comprises the following steps of mixing aniline with aromatic aldehyde, reacting the aniline and the aromatic aldehyde at the room temperature to obtain an intermediate product; dissolving the obtained intermediate product into an organic solvent, adding M-chloroperbenzoic acid, and conducting the reaction at the room temperature, so as to obtain the N-aryl hydroxylamine acid. In comparison with the traditional acyl chloride production methods, the production method provided by the invention has the advantages that the operation condition is milder, the reaction is carried out at the room temperature without rigorous de-watering operations and devices, the separation and purification operations of the obtained intermediate product or final product are simple, and the yield of the final product is as high as 80%, so that the method provided by the invention is suitable for industrial production.

Description

technical field [0001] The invention specifically relates to a synthesis method of N-aryl hydroxylamine acid. Background technique [0002] Hydroxyamic acid and its derivatives are an important class of metal ion chelating agents, which can interact with Cu 2+ 、Co 2+ 、Ni 2+ , Fe 2+ , Zn 2+ and other metal ions to form stable metal chelates. In addition, the hydroxylamine group and the metal ion on the mineral surface form a chelate, which is adsorbed on the mineral surface, making the hydrophobic group float up, thus acting as a collector. It is precisely because of the excellent chelation effect of hydroxylamic acid and its derivatives on metal ions that they can provide a good transport method for metal ions in the human body, so that they have extensive and important applications in chemistry and biochemistry. The method of existing synthetic N-aryl hydroxylamic acid mainly contains following three kinds: [0003] 1. Completed by acetylation of N-aryl hydroxylamine...

Claims

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Application Information

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IPC IPC(8): C07C259/10
Inventor 火星
Owner LANZHOU UNIVERSITY
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