CN107673992A - A kind of ortho-aminophenol Schiff base derivatives and preparation method thereof - Google Patents
A kind of ortho-aminophenol Schiff base derivatives and preparation method thereof Download PDFInfo
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- CN107673992A CN107673992A CN201711106366.7A CN201711106366A CN107673992A CN 107673992 A CN107673992 A CN 107673992A CN 201711106366 A CN201711106366 A CN 201711106366A CN 107673992 A CN107673992 A CN 107673992A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
Abstract
The invention discloses a kind of ortho-aminophenol Schiff base derivatives and preparation method thereof, the structural formula of the Schiff base derivatives is：
Description
Technical field
The invention belongs to organic synthesis field, more particularly to a kind of ortho-aminophenol Schiff base derivatives and its preparation side
Method.
Background technology
Schiff bases is primarily referred to as a kind of organic compound containing imines or azomethine group, typically by containing active carbonyl
Compound and the primary amine condensation of base form.Schiff bases and its complex, have excellent antibacterial, anticancer, antiviral, weeding etc. raw
Thing activity, and the performance such as special photoelectromagnetic.Therefore, draw in recent years in fields such as medicine, biology, catalysis and functional materials
The widely studied interest of researcher is played.
However, the traditional preparation methods of schiff bases be usually in organic solvent, by the compound containing active carbonyl with
Amine carries out condensation reaction and obtained, and reaction needs to use organic solvent, catalyst, and the reaction time is longer, and side reaction is more, and is difficult to
Separating-purifying, there is the deficiencies of power consumption is high, pollution is larger.Therefore, new Schiff base derivatives are developed, and green,
The low preparation method of high-efficient simple, energy consumption is significant.
Publication No. CN106496065A patent of invention discloses a kind of o-phenylenediamine Schiff base derivatives and its preparation
Method, this method is using NPD and benzaldehyde as raw material, by above-mentioned reaction raw materials and in right amount in hydrothermal reaction kettle
Water mixing, reacted under high temperature by the high diffusivity coefficient and strong solubility of high-temperature water.The patented method is without using having
Solvent and catalyst, mild condition, but the o-phenylenediamine Schiff base derivatives low yield prepared, it is typically left 20~30%
It is right.
The content of the invention
For deficiencies of the prior art, it is an object of the invention to provide a kind of ortho-aminophenol schiff bases derivative
Thing and preparation method thereof, solve the problems, such as that existing method prepares Schiff base derivatives and needs to use organic solvent, catalyst.
To achieve the above object, the present invention adopts the following technical scheme that：
Ortho-aminophenol Schiff base derivatives of the present invention, shown in its structural formula such as formula (I)：
The preparation method of ortho-aminophenol Schiff base derivatives is as described above：It is 1 by mol ratio:1~2 2- ammonia
Base -4- nitrophenols and benzaldehyde, which are placed in hydrothermal reaction kettle, to be reacted, wherein, the compactedness of the hydrothermal reaction kettle reclaimed water
For 30~70%, reaction temperature is 90~170 DEG C, and the reaction time be 120~240min, after completion of the reaction, reaction product process
Filter, dry, recrystallization, that is, obtain described ortho-aminophenol Schiff base derivatives.
The reaction equation that the present invention prepares ortho-aminophenol Schiff base derivatives is as follows：
Preferably, the mol ratio of the 2- Amino-4-nitrophenols and benzaldehyde is 1:1.5~2.
Preferably, the reaction temperature is 140~160 DEG C.
Preferably, the reaction time is 150~210min.
Preferably, the compactedness is 50~70%.
Under above-mentioned optimum condition, the yield of Schiff base derivatives prepared by the present invention is greatly improved.
Preferably, ethanol or ethyl acetate that the solvent that recrystallization uses is 95%.The present invention by preferable solvent,
The purity and yield of product can be effectively improved, recrystallization method is conventional method.
Schiff base derivatives prepared by the present invention can be applied in the fields such as medicine, catalysis and functional material.
Compared with prior art, the present invention has the advantages that：
1st, the preparation method of ortho-aminophenol Schiff base derivatives of the present invention replaces Conventional glass instrument with hydrothermal reaction kettle
As reaction unit, high temperature high voltage resistant, conventional organic solvent is replaced as reaction medium using water, it is nontoxic, and without using appointing
What catalyst, reaction raw materials are mixed, be placed in hydrothermal reaction kettle with suitable quantity of water under the subcritical or supercritical temperature of water, main
The high diffusivity coefficient and strong solubility of high-temperature water are utilized, so that reaction is efficient, easily carries out.The preparation method green ring
Protect, mild condition, the reaction time is short, and accessory substance is few and is easily isolated purification, and yield is high, is easy to operate and control, required equipment
It is cheap and raw material is easy to get.
2nd, the Schiff base derivatives that prepare of the present invention, due to the connection of imines both ends it is on the one hand the structure containing phenyl ring,
Chemical stability is good, on the other hand, is dissolved in common a variety of organic solvents, dissolubility is good, and has photoluminescent property, in organic hair
The fields such as optical function material have a good application prospect.
3rd, the present invention reduces the generation of side reaction, significantly by the selection and the optimization of reaction condition to reaction raw materials
The yield of the Schiff base derivatives of preparation is improved, maximum output is up to 64.5%, hence it is evident that prepare higher than existing congenic method
The yield of Schiff base derivatives.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of Schiff base derivatives prepared by embodiment 2；
Fig. 2 is the fluorescence emission spectrogram of compound of Schiff base derivatives prepared by embodiment 2.
Embodiment
The present invention is described in further detail with reference to specific embodiment.
Embodiment 1
In 25mL hydrothermal reaction kettle, add 10mL water (compactedness 40%), add 3mmol 2- amino-
The benzaldehyde of 4- nitrophenols and 3mmol, reacted 240 minutes at 100 DEG C.After reaction terminates, reactor is cooled to room temperature
Afterwards, reaction product filtered successively, dried, being recrystallized, being dried, that is, obtaining target product, being recrystallized in the present embodiment makes
Solvent is 95% ethanol.
Embodiment 2
In 50mL hydrothermal reaction kettle, add 25mL water (compactedness 50%), add 2mmol 2- amino-
4- nitrophenols and 2mmol benzaldehydes, reacted 150 minutes at 120 DEG C.After reaction terminates, after reactor is cooled into room temperature,
Reaction product is filtered successively, dries, recrystallize, is dried, that is, obtains target product, is used when being recrystallized in the present embodiment
Solvent be ethyl acetate.
Embodiment 3
In 50mL hydrothermal reaction kettle, add 30mL water (compactedness 60%), add 1mmol 2- amino-
4- nitrophenols and 1.5mmol benzaldehydes, reacted 120 minutes at 150 DEG C.After reaction terminates, reactor is cooled to room temperature
Afterwards, reaction product filtered successively, dried, being recrystallized, being dried, that is, obtaining target product, being recrystallized in the present embodiment makes
Solvent is ethyl acetate.
Embodiment 4~12
The operating method of embodiment 4~12 is same as Example 1, and difference is design parameter difference, is specifically shown in Table 1.
The relevant parameter of 1 embodiment of table 1~12
By above example, Schiff base derivatives yield prepared by the present invention reaches as high as 64.5%.
Fig. 1 is the infrared spectrogram of ortho-aminophenol Schiff base derivatives prepared by embodiment 2, as seen from the figure, 2- amino-
4- nitrophenols are in 3320cm-1And 3350cm-1Place, be attributed to primary amine N-H telescope features absworption peaks it is reacted after disappear.
The ortho-aminophenol Schiff base derivatives of preparation are in 1630cm-1In the range of occur schiff bases-C=N- groups telescope features inhale
Peak is received, in about 840cm-1And 740cm-1Occur the phenyl ring characteristic absorption peak of contraposition and ortho position substitution respectively, thus illustrate target
Product Schiff base is successfully prepared.
Fig. 2 is the ortho-aminophenol Schiff base derivatives of the preparation of embodiment 2 in tetrahydrofuran (solid line in figure) and anhydrous second
Fluorescence emission spectrogram of compound (excitation wavelength 300nm) in alcohol (dotted line in figure), as shown in Figure 2, adjacent hydroxyl prepared by the present invention
Aniline Schiff base derivatives have certain luminosity in absolute ethyl alcohol and tetrahydrofuran solution, in luminous organic material etc.
There is potential application value in field.
The above embodiment of the present invention is only example to illustrate the invention, and is not the implementation to the present invention
The restriction of mode.For those of ordinary skill in the field, other can also be made not on the basis of the above description
With the change and variation of form.Here all embodiments can not be exhaustive.It is every to belong to technical scheme
Row of the obvious changes or variations amplified out still in protection scope of the present invention.
Claims (7)
- A kind of 1. ortho-aminophenol Schiff base derivatives as shown in formula (I)：
- A kind of 2. method for preparing ortho-aminophenol Schiff base derivatives as claimed in claim 1, it is characterised in that general mole Than for 1:1~2 2- Amino-4-nitrophenols and benzaldehyde, which is placed in hydrothermal reaction kettle, to be reacted, wherein, the hydro-thermal is anti- The compactedness for answering kettle reclaimed water is 30~70%, and reaction temperature is 90~170 DEG C, and the reaction time is 120~240min, and reaction finishes Afterwards, reaction product is filtered, dry, recrystallization, that is, obtains described ortho-aminophenol Schiff base derivatives.
- 3. the preparation method of ortho-aminophenol Schiff base derivatives according to claim 2, it is characterised in that the 2- ammonia The mol ratio of base -4- nitrophenols and benzaldehyde is 1:1.5~2.
- 4. the preparation method of ortho-aminophenol Schiff base derivatives according to claim 2, it is characterised in that the reaction Temperature is 140~160 DEG C.
- 5. the preparation method of ortho-aminophenol Schiff base derivatives according to claim 2, it is characterised in that the reaction Time is 150~210min.
- 6. the preparation method of ortho-aminophenol Schiff base derivatives according to claim 2, it is characterised in that the filling Spend for 50~70%.
- 7. the preparation method of ortho-aminophenol Schiff base derivatives according to claim 2, it is characterised in that recrystallization makes Solvent is 95% ethanol or ethyl acetate.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496065A (en) * | 2016-10-31 | 2017-03-15 | 重庆理工大学 | A kind of o-phenylenediamine Schiff base derivatives and preparation method and application |
| CN106518726A (en) * | 2016-10-31 | 2017-03-22 | 重庆理工大学 | Aryl Schiff base derivative and preparation method and application thereof |
| CN106748879A (en) * | 2016-10-31 | 2017-05-31 | 重庆理工大学 | P-nitrobenzaldehyde Schiff base derivative and preparation method and application thereof |
-
2017
- 2017-11-10 CN CN201711106366.7A patent/CN107673992A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496065A (en) * | 2016-10-31 | 2017-03-15 | 重庆理工大学 | A kind of o-phenylenediamine Schiff base derivatives and preparation method and application |
| CN106518726A (en) * | 2016-10-31 | 2017-03-22 | 重庆理工大学 | Aryl Schiff base derivative and preparation method and application thereof |
| CN106748879A (en) * | 2016-10-31 | 2017-05-31 | 重庆理工大学 | P-nitrobenzaldehyde Schiff base derivative and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| STEPHENS, F. F.等: "Preparation of benzimidazoles and benzoxazoles from Schiff"s bases. II", 《JOURNAL OF THE CHEMICAL SOCIETY》 * |
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