CN107488127A - The method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent - Google Patents
The method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent Download PDFInfo
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- CN107488127A CN107488127A CN201610422727.8A CN201610422727A CN107488127A CN 107488127 A CN107488127 A CN 107488127A CN 201610422727 A CN201610422727 A CN 201610422727A CN 107488127 A CN107488127 A CN 107488127A
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- sodium dithionite
- aminobenzaldehyde
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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Abstract
This application discloses a kind of method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent, and using o-nitrobenzaldehyde as initiation material, using sodium dithionite as reducing agent, o-Aminobenzaldehyde is prepared by carrying out reduction reaction to o-nitrobenzaldehyde.The present invention synthesizes o-Aminobenzaldehyde, high income, and green non-pollution by reducing agent of sodium dithionite.
Description
Technical field
The application is related to a kind of method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent.
Background technology
O-Aminobenzaldehyde is important intermediate, is widely used in fine chemistry industry and field of medicaments.In medicine, it
2- amino -3,5 dibromo benzaldehydes can be further synthesized, and it is as the highly important of synthesis ambroxol (ambroxol)
Intermediate.Ambroxol is the exploitation listing first in 1984 of German BoehringerIngelheim companies, is permitted as the world
A kind of good eliminating the phlegm new drug that more state approvals use, the usage amount in current medicine are considerable.From ortho-methylnitrobenzene
One-step synthesis o-Aminobenzaldehyde, medicine intermediate green syt is explored, reducing product cost just turns into the popular class of researcher
Topic.According to document report in recent years, Chinese and overseas scholars in para aminotenzaldehyde one-step synthesis research comparative maturity, obtain 90% with
On higher yield, but the one-step synthesis in o-Aminobenzaldehyde is to make slow progress, and document report only has trivial 8%
Yield (document：Synthesis, 1978 (1), 23-4.), therefore the actual synthesis o-Aminobenzaldehyde produced greatly, all pass through
What multistep reaction could be realized, thus during used the reagent of excess, the longer reaction time, harsh reaction condition and
The use of a large amount of solvents, and yield is poor, the theory of this and Green Chemistry mutually deviates from, and cost is at a relatively high.
The content of the invention
It is an object of the invention to provide it is a kind of using sodium dithionite as reducing agent synthesize o-Aminobenzaldehyde method,
To overcome deficiency of the prior art.
To achieve the above object, the present invention provides following technical scheme：
The embodiment of the present application discloses a kind of method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent, with neighbour
Nitrobenzaldehyde is initiation material, using sodium dithionite as reducing agent, by carrying out reduction reaction system to o-nitrobenzaldehyde
Standby o-Aminobenzaldehyde.
Preferably, in the above-mentioned method using sodium dithionite as reducing agent synthesis o-Aminobenzaldehyde, including：
(1), o-nitrobenzaldehyde and tetrahydrofuran are thoroughly mixed；
(2), the mixed solution of sodium dithionite and water is added dropwise in reaction system under stirring, then proceeded to
The stirring reaction at 40~50 DEG C, extent of reaction is tracked with high performance liquid chromatography (HPLC)；
(3) reaction solution, is extracted with ethyl acetate in reaction solution, merges organic layer；
(4) organic layer, is washed till neutrality with water, stratification obtains organic phase；
(5), product is obtained after removing ethyl acetate with anhydrous sodium sulfate drying, filtering, filtrate revolving.
Preferably, in the above-mentioned method using sodium dithionite as reducing agent synthesis o-Aminobenzaldehyde, the step
Suddenly in (1), the temperature being stirred is 10~13 DEG C.
Preferably, in the above-mentioned method using sodium dithionite as reducing agent synthesis o-Aminobenzaldehyde, the step
Suddenly in (2), the time that the mixed solution of sodium dithionite and water is added dropwise is 2~2.5 hours.
Preferably, in the above-mentioned method using sodium dithionite as reducing agent synthesis o-Aminobenzaldehyde, the step
Suddenly in (2), the time of stirring reaction is 2~3 hours.
Preferably, in the above-mentioned method using sodium dithionite as reducing agent synthesis o-Aminobenzaldehyde, the neighbour
The ratio of nitrobenzaldehyde and tetrahydrofuran is (1.1~1.2):1.
Preferably, in the above-mentioned method using sodium dithionite as reducing agent synthesis o-Aminobenzaldehyde, the company
In the mixed solution of sodium sulfite and water, the mol ratio of sodium dithionite and water is (1.1~1.2):1.
Compared with prior art, the advantage of the invention is that：
The present invention synthesizes o-Aminobenzaldehyde, high income, and green non-pollution by reducing agent of sodium dithionite.
Embodiment
The present invention is described further by the following example：According to following embodiments, the present invention may be better understood.
However, as it will be easily appreciated by one skilled in the art that specific material ratio, process conditions and its result described by embodiment are only used
In the explanation present invention, without should be also without limitation on the present invention described in detail in claims.
Embodiment 1
1st, o-nitrobenzaldehyde and tetrahydrofuran are thoroughly mixed at 10 DEG C；
2nd, the mixed solution of sodium dithionite and water is added dropwise in reaction system under stirring, time for adding is
2 hours, stirring reaction 2 hours at 50 DEG C are then proceeded to, extent of reaction is tracked with high performance liquid chromatography (HPLC)；
3rd, reaction solution is extracted with ethyl acetate in reaction solution, merges organic layer；
4th, organic layer is washed till neutrality with water, stratification obtains organic phase；
5th, product is obtained after removing ethyl acetate with anhydrous sodium sulfate drying, filtering, filtrate revolving.
In the present embodiment, the ratio of o-nitrobenzaldehyde and tetrahydrofuran is 1:1；The mixing of sodium dithionite and water is molten
In liquid, the mol ratio of sodium dithionite and water is 1.2:1.
Obtain the yield 86% of product, content 96.4% (HPLC detections).
Embodiment 2
1st, o-nitrobenzaldehyde and tetrahydrofuran are thoroughly mixed at 10 DEG C；
2nd, the mixed solution of sodium dithionite and water is added dropwise in reaction system under stirring, time for adding is
1.5 hours, stirring reaction 2 hours at 45 DEG C are then proceeded to, extent of reaction is tracked with high performance liquid chromatography (HPLC)；
3rd, reaction solution is extracted with ethyl acetate in reaction solution, merges organic layer；
4th, organic layer is washed till neutrality with water, stratification obtains organic phase；
5th, product is obtained after removing ethyl acetate with anhydrous sodium sulfate drying, filtering, filtrate revolving.
In the present embodiment, the ratio of o-nitrobenzaldehyde and tetrahydrofuran is 1.1:1；The mixing of sodium dithionite and water
In solution, the mol ratio of sodium dithionite and water is 1.1:1.
Obtain the yield 86.5% of product, content 96.8% (HPLC detections).
Embodiment 3
1st, o-nitrobenzaldehyde and tetrahydrofuran are thoroughly mixed at 10 DEG C；
2nd, the mixed solution of sodium dithionite and water is added dropwise in reaction system under stirring, time for adding is
1.8 hours, stirring reaction 2 hours at 48 DEG C are then proceeded to, extent of reaction is tracked with high performance liquid chromatography (HPLC)；
3rd, reaction solution is extracted with ethyl acetate in reaction solution, merges organic layer；
4th, organic layer is washed till neutrality with water, stratification obtains organic phase；
5th, product is obtained after removing ethyl acetate with anhydrous sodium sulfate drying, filtering, filtrate revolving.
In the present embodiment, the ratio of o-nitrobenzaldehyde and tetrahydrofuran is 1.2:1；The mixing of sodium dithionite and water
In solution, the mol ratio of sodium dithionite and water is 1.2:1.
Obtain the yield 87.1% of product, content 97.2% (HPLC detections).
Finally, it is to be noted that, term " comprising ", "comprising" or its any other variant be intended to it is non-exclusive
Property includes, so that process, method, article or equipment including a series of elements not only include those key elements, and
Also include the other element that is not expressly set out, or also include for this process, method, article or equipment inherently
Key element.
Claims (7)
- A kind of 1. method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent, it is characterised in that：With ortho-nitrophenyl Formaldehyde is initiation material, and using sodium dithionite as reducing agent, adjacent ammonia is prepared by carrying out reduction reaction to o-nitrobenzaldehyde Benzaldehyde.
- 2. the method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent according to right will go 1, its feature It is, including：(1), o-nitrobenzaldehyde and tetrahydrofuran are thoroughly mixed；(2), the mixed solution of sodium dithionite and water is added dropwise in reaction system under stirring, then proceeded to 40 Stirring reaction at~50 DEG C, extent of reaction is tracked with high performance liquid chromatography (HPLC)；(3) reaction solution, is extracted with ethyl acetate in reaction solution, merges organic layer；(4) organic layer, is washed till neutrality with water, stratification obtains organic phase；(5), product is obtained after removing ethyl acetate with anhydrous sodium sulfate drying, filtering, filtrate revolving.
- 3. the method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent according to right will go 2, its feature It is：In the step (1), the temperature being stirred is 10~13 DEG C.
- 4. the method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent according to right will go 2, its feature It is：In the step (2), the time that the mixed solution of sodium dithionite and water is added dropwise is 2~2.5 hours.
- 5. the method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent according to right will go 2, its feature It is：In the step (2), the time of stirring reaction is 2~3 hours.
- 6. the method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent according to right will go 2, its feature It is：The ratio of the o-nitrobenzaldehyde and tetrahydrofuran is (1.1~1.2):1.
- 7. the method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent according to right will go 2, its feature It is：In the mixed solution of the sodium dithionite and water, the mol ratio of sodium dithionite and water is (1.1~1.2):1.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610422727.8A CN107488127A (en) | 2016-06-13 | 2016-06-13 | The method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent |
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| CN201610422727.8A CN107488127A (en) | 2016-06-13 | 2016-06-13 | The method that o-Aminobenzaldehyde is synthesized using sodium dithionite as reducing agent |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101735023A (en) * | 2008-11-24 | 2010-06-16 | 联化科技股份有限公司 | Method for preparing 3-bromo-5-chlorophenol |
| CN103391924A (en) * | 2010-11-15 | 2013-11-13 | 鲁汶天主教大学 | Novel antiviral compounds |
-
2016
- 2016-06-13 CN CN201610422727.8A patent/CN107488127A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101735023A (en) * | 2008-11-24 | 2010-06-16 | 联化科技股份有限公司 | Method for preparing 3-bromo-5-chlorophenol |
| CN103391924A (en) * | 2010-11-15 | 2013-11-13 | 鲁汶天主教大学 | Novel antiviral compounds |
Non-Patent Citations (1)
| Title |
|---|
| GALIA MAAYAN等: "Stabilization of unique valencies of cobalt, nickel and copper by complexation with the tridentate ligand 2-(2’-pyridyl)-8-hydroxyquinoline", 《POLYHEDRON》 * |
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Application publication date: 20171219 |