CN107488126A - The method that the dibromo benzaldehyde of 2 amino 3,5 is synthesized by hydrogen peroxide - Google Patents
The method that the dibromo benzaldehyde of 2 amino 3,5 is synthesized by hydrogen peroxide Download PDFInfo
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- CN107488126A CN107488126A CN201610422413.8A CN201610422413A CN107488126A CN 107488126 A CN107488126 A CN 107488126A CN 201610422413 A CN201610422413 A CN 201610422413A CN 107488126 A CN107488126 A CN 107488126A
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- 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
The method for synthesizing the dibromo benzaldehyde of 2 amino 3,5 by hydrogen peroxide this application discloses one kind, using reduction reaction product o-Aminobenzaldehyde and bromine as raw material, by the way that the hydrogen peroxide of bromine utilization rate can be improved, prepare the synthesis dibromo benzaldehyde of 2 amino 3,5.The present invention synthesizes the dibromo benzaldehyde of 2 amino 3,5, high income, and green non-pollution by that can improve the dioxygen water additive of bromine utilization rate.
Description
Technical field
The application is related to a kind of method that the dibromo benzaldehyde of 2- amino -3,5 is synthesized by hydrogen peroxide.
Background technology
2- amino -3,5- dibromo benzaldehydes are a kind of conventional pharmaceutical intermediates, are widely used in expelling phlegm drugses hydrochloric acid ammonia bromine
The synthesis of rope.The route of synthesis of ambroxol hydrochloride is a lot, but most widely used approach is：With 2- amino -3,5- dibromos
Benzaldehyde is raw material, with it is trans-condensation carried out to aminocyclohexanol form intermediate imine class product, then by hydro-reduction with
And acidifying obtains ambroxol hydrochloride into salt.As the important intermediate of ambroxol hydrochloride, 2- amino -3,5- dibromo benzaldehyde tool
There is larger demand.
The process yield of existing synthesis 2- amino -3,5- dibromo benzaldehydes is relatively low, complex process.
The content of the invention
It is an object of the invention to provide one kind by hydrogen peroxide synthesize 2- amino -3,5 dibromo benzaldehydes method, with gram
Take 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 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, anti-to reduce
It is raw material to answer product o-Aminobenzaldehyde and bromine, by that can improve the hydrogen peroxide of bromine utilization rate, prepares synthesis 2- amino -3,
5 dibromo benzaldehydes.
Preferably, in the above-mentioned method that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, including step：
(1), ethanol and o-Aminobenzaldehyde are uniformly mixed；
(2), agitation and dropping bromine and 30% hydrogen peroxide into reaction solution；
(3), stirring reaction 30 minutes at a temperature of 5~20 DEG C；
(4), continue to add excessive saturated sodium bicarbonate solution into reaction solution, be sufficiently stirred, until solid separates out, mistake
Filter obtains the dibromo benzaldehyde of 2- amino -3,5.
Preferably, in the above-mentioned method that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, the step (1)
In, the mol ratio 5 of ethanol and o-Aminobenzaldehyde:1.
Preferably, in the above-mentioned method that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, the step (2)
In, the mol ratio of o-Aminobenzaldehyde, bromine and KBr is 1:1.93:9.5.
Preferably, in the above-mentioned method that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, the step (2)
In, time for adding is 10~30 minutes.
Preferably, in the above-mentioned method that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, the step (2)
In, the mol ratio of bromine and hydrogen peroxide is 1.2:1.
Compared with prior art, the advantage of the invention is that：The present invention is added by that can improve the hydrogen peroxide of bromine utilization rate
Agent is added to synthesize 2- amino -3,5 dibromo benzaldehydes, high income, and green non-pollution.
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
The synthetic method of 2- amino -3,5 dibromo benzaldehydes, including：
(1), by ethanol and o-Aminobenzaldehyde according to mol ratio 5:1 is uniformly mixed；
(2), agitation and dropping bromine and 30% hydrogen peroxide, wherein o-Aminobenzaldehyde, bromine and bromination into reaction solution
The mol ratio of potassium is 1:1.93:9.5, time for adding is 10 minutes, and the mol ratio of bromine and hydrogen peroxide is 1.2:1；
(3), stirring reaction 30 minutes at a temperature of 5 DEG C, extent of reaction is tracked with high performance liquid chromatography (HPLC)；
(4), continue to add excessive saturated sodium bicarbonate solution into reaction solution, be sufficiently stirred, until solid separates out, mistake
Filter obtains the dibromo benzaldehyde of 2- amino -3,5.
The dibromo benzaldehyde yield of 2- amino -3,5 is 75.7%.
Embodiment 2
The synthetic method of 2- amino -3,5 dibromo benzaldehydes, including：
(1), by ethanol and o-Aminobenzaldehyde according to mol ratio 5.4:1 is uniformly mixed；
(2), agitation and dropping bromine and 30% hydrogen peroxide, wherein o-Aminobenzaldehyde, bromine and bromination into reaction solution
The mol ratio of potassium is 1:1.94:9.6, time for adding is 20 minutes, and the mol ratio of bromine and hydrogen peroxide is 1.2:1；
(3), stirring reaction 30 minutes at a temperature of 10 DEG C, extent of reaction is tracked with high performance liquid chromatography (HPLC)；
(4), continue to add excessive saturated sodium bicarbonate solution into reaction solution, be sufficiently stirred, until solid separates out, mistake
Filter obtains the dibromo benzaldehyde of 2- amino -3,5.
The dibromo benzaldehyde yield of 2- amino -3,5 is 73.8%.
Embodiment 3
The synthetic method of 2- amino -3,5 dibromo benzaldehydes, including：
(1), by ethanol and o-Aminobenzaldehyde according to mol ratio 5:1 is uniformly mixed；
(2), agitation and dropping bromine and 30% hydrogen peroxide, wherein o-Aminobenzaldehyde, bromine and bromination into reaction solution
The mol ratio of potassium is 1:1.91:9.2, time for adding is 30 minutes, and the mol ratio of bromine and hydrogen peroxide is 1.2:1；
(3), stirring reaction 30 minutes at a temperature of 20 DEG C, extent of reaction is tracked with high performance liquid chromatography (HPLC)；
(4), continue to add excessive saturated sodium bicarbonate solution into reaction solution, be sufficiently stirred, until solid separates out, mistake
Filter obtains the dibromo benzaldehyde of 2- amino -3,5.
The dibromo benzaldehyde yield of 2- amino -3,5 is 74.1%.
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 (6)
- A kind of 1. method that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, it is characterised in that：With reduction reaction product O-Aminobenzaldehyde and bromine are raw material, by that can improve the hydrogen peroxide of bromine utilization rate, prepare synthesis 2- amino -3,5 dibromos Benzaldehyde.
- 2. the method according to claim 1 that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, it is characterised in that Including step：(1), ethanol and o-Aminobenzaldehyde are uniformly mixed；(2), agitation and dropping bromine and 30% hydrogen peroxide into reaction solution；(3), stirring reaction 30 minutes at a temperature of 5~20 DEG C；(4), continue to add excessive saturated sodium bicarbonate solution into reaction solution, be sufficiently stirred, until solid separates out, filtering obtains Obtain the dibromo benzaldehyde of 2- amino -3,5.
- 3. the method according to claim 2 that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, it is characterised in that： In the step (1), the mol ratio 5 of ethanol and o-Aminobenzaldehyde:1.
- 4. the method according to claim 2 that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, it is characterised in that： In the step (2), the mol ratio of o-Aminobenzaldehyde, bromine and KBr is 1:1.93:9.5.
- 5. the method according to claim 2 that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, it is characterised in that： In the step (2), time for adding is 10~30 minutes.
- 6. the method according to claim 2 that 2- amino -3,5 dibromo benzaldehydes are synthesized by hydrogen peroxide, it is characterised in that： In the step (2), the mol ratio of bromine and hydrogen peroxide is 1.2:1.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610422413.8A CN107488126A (en) | 2016-06-13 | 2016-06-13 | The method that the dibromo benzaldehyde of 2 amino 3,5 is synthesized by hydrogen peroxide |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610422413.8A CN107488126A (en) | 2016-06-13 | 2016-06-13 | The method that the dibromo benzaldehyde of 2 amino 3,5 is synthesized by hydrogen peroxide |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113444004A (en) * | 2021-06-29 | 2021-09-28 | 江西荣兴药业有限公司 | Production process of 3, 5-dibromo anthranilic aldehyde |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2025939A (en) * | 1978-04-20 | 1980-01-30 | Boehringer Sohn Ingelheim | Processes for the preparation of sulphur-containing n-benzyl-amino acids |
| CN102351720A (en) * | 2011-10-21 | 2012-02-15 | 南京理工大学 | Simple and efficient ambroxol synthesis method |
| CN104447366A (en) * | 2014-12-25 | 2015-03-25 | 江西荣兴药业有限公司 | Preparation method of high-purity 2-amino-3, 5-dibromobenzaldehyde |
-
2016
- 2016-06-13 CN CN201610422413.8A patent/CN107488126A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2025939A (en) * | 1978-04-20 | 1980-01-30 | Boehringer Sohn Ingelheim | Processes for the preparation of sulphur-containing n-benzyl-amino acids |
| CN102351720A (en) * | 2011-10-21 | 2012-02-15 | 南京理工大学 | Simple and efficient ambroxol synthesis method |
| CN104447366A (en) * | 2014-12-25 | 2015-03-25 | 江西荣兴药业有限公司 | Preparation method of high-purity 2-amino-3, 5-dibromobenzaldehyde |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113444004A (en) * | 2021-06-29 | 2021-09-28 | 江西荣兴药业有限公司 | Production process of 3, 5-dibromo anthranilic aldehyde |
| CN113444004B (en) * | 2021-06-29 | 2023-06-23 | 江西荣兴药业有限公司 | 3, 5-dibromo-o-amino benzaldehyde production process |
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Application publication date: 20171219 |
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