Method for synthesizing o-aminobenzaldehyde

A technology for o-aminobenzaldehyde and o-nitrobenzaldehyde is applied in the field of synthesizing o-aminobenzaldehyde and pharmaceutical intermediates, and can solve the problems of low conversion rate, low efficiency of reducing agent use, etc., and achieve high conversion rate and high efficiency. selective effect

Inactive Publication Date: 2016-01-20
LIANYUNGANG RES INST NANJING UNIV OF SCI & TECH
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  • Abstract
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Problems solved by technology

In the first two methods, the use efficiency of the reducing agent is low; while iron powder can generally be used in the selective reduction pharmaceutical industry, and is often used as a reducing agent for nitro compounds, but its conversion rate is not high, and a large amount of waste water will be generated and iron sludge, and people have not been able to deal with these pollutions well

Method used

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  • Method for synthesizing o-aminobenzaldehyde

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] In the first step, 30mg of 5wt% Pd / C catalyst, 0.9g of o-nitrobenzaldehyde, 40mL of methanol and 5mL of water were added into the autoclave.

[0022] In the second step, in the autoclave, with N 2 Replace 3 times, pass H 2 , to H 2 The partial pressure is 1.5 MPa, the reaction temperature is 70° C., and the reaction time is 5 hours, so that o-nitrobenzaldehyde is converted into anthranilaldehyde.

[0023] The third step is to cool the reactor to room temperature, filter out the catalyst, wash the separated catalyst with absolute ethanol, soak it in absolute ethanol after washing, and prepare for repeated use; then extract the filtrate with dichloromethane for 3-4 times , combined the organic layers, dried with anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane to obtain the anthranilaldehyde product.

[0024] According to high-performance liquid chromatography analysis, the conversion rate of o-nitrobenzaldehyde is 90...

Embodiment 2

[0026] In the first step, 30mg of 5wt% Pd / C catalyst, 0.9g of o-nitrobenzaldehyde, 40mL of ethanol, and 5mL of water were added into the autoclave.

[0027] In the second step, in the autoclave, with N 2 Replace 3 times, pass H 2 , to H 2 The partial pressure is 2.0 MPa, the reaction temperature is 80° C., and the reaction time is 6 hours, so that o-nitrobenzaldehyde is converted into anthranilaldehyde.

[0028] The third step is to cool the reactor to room temperature, filter out the catalyst, wash the separated catalyst with absolute ethanol, soak it in absolute ethanol after washing, and prepare for repeated use; then extract the filtrate with dichloromethane for 3-4 times , combined the organic layers, dried with anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane to obtain the anthranilaldehyde product.

[0029] According to high-performance liquid chromatography analysis, the conversion rate of o-nitrobenzaldehyde is 90...

Embodiment 3

[0031] In the first step, 30mg of 5wt% Pd / C catalyst, 0.9g of o-nitrobenzaldehyde, 40mL of n-propanol, and 5mL of water were added into the autoclave.

[0032] In the second step, in the autoclave, with N 2 Replace 3 times, pass H 2 , to H 2 The partial pressure is 2.0 MPa, the reaction temperature is 90° C., and the reaction time is 8 hours, so that o-nitrobenzaldehyde is converted into anthranilaldehyde.

[0033] The third step is to cool the reactor to room temperature, filter out the catalyst, wash the separated catalyst with absolute ethanol, soak it in absolute ethanol after washing, and prepare for repeated use; then extract the filtrate with dichloromethane for 3-4 times , combined the organic layers, dried with anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane to obtain the anthranilaldehyde product.

[0034] According to high-performance liquid chromatography analysis, the conversion rate of o-nitrobenzaldehyde is...

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Abstract

The invention discloses a method for synthesizing o-aminobenzaldehyde. The method comprises the following steps: adding a Pd / C or Ni / C catalyst into a mixed solvent containing o-nitrobenzaldehyde; replacing air in a high-pressure reaction kettle with N2, and introducing H2 to react at 50-120 DEG C for 5-10 hours; filtering reaction liquid, and analyzing filtrate by virtue of a high performance liquid chromatography, wherein the conversion rate and the selectivity can reach 90% or more. According to the method, the catalyst can be recycled after the reaction; no waste liquid and waste residue is emitted in the reaction process; aldehyde is not reduced when nitryl is reduced.

Description

technical field [0001] The invention relates to the synthesis of a pharmaceutical intermediate, in particular to a method for synthesizing anthranilaldehyde, which belongs to the field of organic chemistry. Background technique [0002] Anthranilbenzaldehyde is a commonly used intermediate in organic synthesis, raw materials for dyestuffs and pharmaceutical raw materials, and is an important raw material for the synthesis of quinoline anti-inflammatory and antiviral drugs. [0003] At present, its industrial production method has: (1) Na 2 S 2 o 4 Reduction method; (2) FeSO 4 ·7H 2 O+NH 3 ·H 2 O reduction method; (3) Iron powder reduction method. In the first two methods, the use efficiency of the reducing agent is low; while iron powder can generally be used in the selective reduction pharmaceutical industry, and is often used as a reducing agent for nitro compounds, but its conversion rate is not high, and a large amount of waste water will be generated and iron sl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C223/06C07C221/00
CPCY02P20/584
Inventor 刘顺强蒋志斌彭新华
Owner LIANYUNGANG RES INST NANJING UNIV OF SCI & TECH
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