CN107488122A - A kind of synthetic method of ortho-methylnitrobenzene aldehyde - Google Patents
A kind of synthetic method of ortho-methylnitrobenzene aldehyde Download PDFInfo
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- CN107488122A CN107488122A CN201610414456.1A CN201610414456A CN107488122A CN 107488122 A CN107488122 A CN 107488122A CN 201610414456 A CN201610414456 A CN 201610414456A CN 107488122 A CN107488122 A CN 107488122A
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- methylnitrobenzene
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- aldehyde
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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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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
This application discloses a kind of synthetic method of ortho-methylnitrobenzene aldehyde, using o-nitrobenzaldehyde as initiation material, with FeSO4·7H2O is reducing agent, and o-Aminobenzaldehyde is prepared by carrying out reduction reaction to o-nitrobenzaldehyde.The present invention is with FeSO4·7H2O is that reducing agent synthesizes o-Aminobenzaldehyde, high income, and green non-pollution.
Description
Technical field
The application is related to a kind of synthetic method of ortho-methylnitrobenzene aldehyde.
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 a kind of synthetic method of o-Aminobenzaldehyde, with overcome it is of the prior art not
Foot.
To achieve the above object, the present invention provides following technical scheme：
The embodiment of the present application discloses a kind of synthetic method of ortho-methylnitrobenzene aldehyde, using o-nitrobenzaldehyde as initiation material,
With FeSO4·7H2O is reducing agent, and o-Aminobenzaldehyde is prepared by carrying out reduction reaction to o-nitrobenzaldehyde.
Preferably, in the synthetic method of above-mentioned ortho-methylnitrobenzene aldehyde, including step：
(1), by ortho-methylnitrobenzene aldehyde and FeSO4·7H2O and the aqueous solution are thoroughly mixed；
(2) concentrated hydrochloric acid, is added dropwise, continues to stir and is warming up to 80~90 DEG C；
(3) ammoniacal liquor, is added dropwise, continues stirring reaction certain time；
(4) steam distillation, is carried out to reaction solution and obtains cut, cut is added in the saturated brine of cooling, is separated out brilliant
Body.
Preferably, in the synthetic method of above-mentioned ortho-methylnitrobenzene aldehyde, in the step (2), during the dropwise addition of concentrated hydrochloric acid
Between be 10~15 minutes.
Preferably, in the synthetic method of above-mentioned ortho-methylnitrobenzene aldehyde, in the step (3), the temperature of stirring reaction
For 80~90 DEG C, the stirring reaction time is 20~30 minutes.
Preferably, in the synthetic method of above-mentioned ortho-methylnitrobenzene aldehyde, the ortho-methylnitrobenzene aldehyde and FeSO4·7H2O
Mol ratio be 1:15~20.
Preferably, in the synthetic method of above-mentioned ortho-methylnitrobenzene aldehyde, the mol ratio of the aqueous solution and ammoniacal liquor is：2
~3:1.
Compared with prior art, the advantage of the invention is that：
The present invention is with FeSO4·7H2O is that reducing agent synthesizes o-Aminobenzaldehyde, 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
1st, by ortho-methylnitrobenzene aldehyde and FeSO4·7H2O and the aqueous solution are thoroughly mixed；
2nd, concentrated hydrochloric acid 10 minutes is added dropwise, continues to stir and is warming up to 90 DEG C；
3rd, ammoniacal liquor is added dropwise, continues stirring reaction 20 minutes under 90 DEG C of temperature conditionss, with high performance liquid chromatography (HPLC) with
Track extent of reaction；
4th, steam distillation is carried out to reaction solution and obtains cut, cut is added in the saturated brine of cooling, separate out crystal.
Its fusing point is surveyed as 35~36 DEG C with melting point apparatus.
In the present embodiment, ortho-methylnitrobenzene aldehyde and FeSO4·7H2O mol ratio is 1:17；Mole of the aqueous solution and ammoniacal liquor
Than for：3:1.
Yield 91%, content 95% (HPLC detections).
Embodiment 2
1st, by ortho-methylnitrobenzene aldehyde and FeSO4·7H2O and the aqueous solution are thoroughly mixed；
2nd, concentrated hydrochloric acid 15 minutes is added dropwise, continues to stir and is warming up to 90 DEG C；
3rd, ammoniacal liquor is added dropwise, continues stirring reaction 30 minutes under 90 DEG C of temperature conditionss, with high performance liquid chromatography (HPLC) with
Track extent of reaction；
4th, steam distillation is carried out to reaction solution and obtains cut, cut is added in the saturated brine of cooling, separate out crystal.
Its fusing point is surveyed as 35~36 DEG C with melting point apparatus.
In the present embodiment, ortho-methylnitrobenzene aldehyde and FeSO4·7H2O mol ratio is 1:15；Mole of the aqueous solution and ammoniacal liquor
Than for：2:1.
Yield 90.5%, content 94% (HPLC detections).
Embodiment 3
1st, by ortho-methylnitrobenzene aldehyde and FeSO4·7H2O and the aqueous solution are thoroughly mixed；
2nd, concentrated hydrochloric acid 12 minutes is added dropwise, continues to stir and is warming up to 80 DEG C；
3rd, ammoniacal liquor is added dropwise, continues stirring reaction 20 minutes under 80 DEG C of temperature conditionss, with high performance liquid chromatography (HPLC) with
Track extent of reaction；
4th, steam distillation is carried out to reaction solution and obtains cut, cut is added in the saturated brine of cooling, separate out crystal.
Its fusing point is surveyed as 35~36 DEG C with melting point apparatus.
In the present embodiment, ortho-methylnitrobenzene aldehyde and FeSO4·7H2O mol ratio is 1:20；Mole of the aqueous solution and ammoniacal liquor
Than for：2.6:1.
Yield 89%, content 93% (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 (6)
- A kind of 1. synthetic method of ortho-methylnitrobenzene aldehyde, it is characterised in that：Using o-nitrobenzaldehyde as initiation material, with FeSO4· 7H2O is reducing agent, and o-Aminobenzaldehyde is prepared by carrying out reduction reaction to o-nitrobenzaldehyde.
- 2. the synthetic method of ortho-methylnitrobenzene aldehyde according to claim 1, it is characterised in that including step：(1), by ortho-methylnitrobenzene aldehyde and FeSO4·7H2O and the aqueous solution are thoroughly mixed；(2) concentrated hydrochloric acid, is added dropwise, continues to stir and is warming up to 80~90 DEG C；(3) ammoniacal liquor, is added dropwise, continues stirring reaction certain time；(4) steam distillation, is carried out to reaction solution and obtains cut, cut is added in the saturated brine of cooling, separates out crystal.
- 3. the synthetic method of ortho-methylnitrobenzene aldehyde according to claim 2, it is characterised in that：In the step (2), dense salt The time for adding of acid is 10~15 minutes.
- 4. the synthetic method of ortho-methylnitrobenzene aldehyde according to claim 2, it is characterised in that：In the step (3), stirring The temperature of reaction is 80~90 DEG C, and the stirring reaction time is 20~30 minutes.
- 5. the synthetic method of ortho-methylnitrobenzene aldehyde according to claim 2, it is characterised in that：The ortho-methylnitrobenzene aldehyde with FeSO4·7H2O mol ratio is 1:15~20.
- 6. the synthetic method of ortho-methylnitrobenzene aldehyde according to claim 2, it is characterised in that：The aqueous solution and ammoniacal liquor Mol ratio is：2~3:1.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610414456.1A CN107488122A (en) | 2016-06-13 | 2016-06-13 | A kind of synthetic method of ortho-methylnitrobenzene aldehyde |
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| CN201610414456.1A CN107488122A (en) | 2016-06-13 | 2016-06-13 | A kind of synthetic method of ortho-methylnitrobenzene aldehyde |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105254516A (en) * | 2015-11-05 | 2016-01-20 | 南京理工大学连云港研究院 | Method for synthesizing o-aminobenzaldehyde |
| CN105295006A (en) * | 2015-09-16 | 2016-02-03 | 南京邮电大学 | Fluorenyl polymer-iridium complex soft salt and preparation and application thereof |
-
2016
- 2016-06-13 CN CN201610414456.1A patent/CN107488122A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105295006A (en) * | 2015-09-16 | 2016-02-03 | 南京邮电大学 | Fluorenyl polymer-iridium complex soft salt and preparation and application thereof |
| CN105254516A (en) * | 2015-11-05 | 2016-01-20 | 南京理工大学连云港研究院 | Method for synthesizing o-aminobenzaldehyde |
Non-Patent Citations (3)
| Title |
|---|
| CHIEN T. C.等: ""1-(2-Quinolyl)-2-naphthol: A new intra-intermolecular photoacid–photobase molecule"", 《JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A: CHEMISTRY》 * |
| D. SAKTHILATHA AND R. RAJAVEL: ""Synthesis, Characterization and Biological Studies of Homobimetallic Schiff Base Cu(II) and Ni(II) Complexes"", 《CHEM SCI TRANS.》 * |
| LEE IRVIN SMITH AND J. W. OPIE: ""o-AMINOBENZALDEHYDE"", 《ORGANIC SYNTHESES》 * |
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Application publication date: 20171219 |