CN105585519A - Preparation method of novel Schiff base micromolecular compound - Google Patents
Preparation method of novel Schiff base micromolecular compound Download PDFInfo
- Publication number
- CN105585519A CN105585519A CN201510667245.4A CN201510667245A CN105585519A CN 105585519 A CN105585519 A CN 105585519A CN 201510667245 A CN201510667245 A CN 201510667245A CN 105585519 A CN105585519 A CN 105585519A
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- CN
- China
- Prior art keywords
- carbazole
- preparation
- schiff bases
- micromolecular compound
- aniline
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
Abstract
The invention provides a preparation method of a novel Schiff base micromolecular compound. The preparation method includes the steps that p-fluoronitrobenzene and carbazole react to prepare 4-carbazole-nitrobenzene, then hydrazine hydrate is used as a reducing agent and palladium on carbon is used as a catalyst to prepare 4-carbazole-aniline, and finally p-aminophenyl carbazole and N,N-ethyl cacodylic acid diacetate benzaldehyde are condensed to prepare Schiff base micromolecules I. The structure of the micromolecules I is shown in the description.
Description
Technical field
The present invention relates to novel schiff bases micromolecular compound and preparation method thereof, belong to organic synthesis field.
Background technology
Aldehyde (ketone) reacts cancellation a part water with amine be to prepare the most classical method of schiff bases, in the process of reaction, can, by removing the water generating in course of reaction or adding acidic catalyst to increase the carrying out of reaction, improve productive rate.
Schiff base compounds and metal complex have important application in medical science, catalysis, analytical chemistry, corrosion and photochromic field. In analytical chemistry, many schiff base compounds can be used to detect or differentiate metal ion, reach the quantitative analysis to some ion by means such as chromatography, fluorescence analysis, photometric analysis. According to schiff base compound structural analysis provided by the invention, this compound has feasibility by fluorescence analysis for the detection of some metal ion.
Summary of the invention
The invention provides a kind of preparation method of novel schiff bases micromolecular compound.
Technical scheme of the present invention is as follows:
A kind of schiff bases micromolecular compound, has the structure of following formula I:
Novel schiff bases micromolecular compound of the present invention be by 4-carbazole-aniline andN,NPrepared by the schiff base reaction of-ethyl diacetate benzaldehyde.
The micromolecular preparation method of schiff bases with formula I structure, step is as follows:
Synthesizing of a, 4-carbazole-nitrobenzene
A certain amount of p-fluoronitrobenzene, carbazole and potash are added in there-necked flask, then add organic solvent DMF, under nitrogen protection, be warming up to boiling, stir 12h, be cooled to room temperature, reactant is poured in frozen water and washed
Wash, suction filtration, benzene recrystallization, vacuum drying, obtains yellow crystals
Synthesizing of b, 4-carbazole-aniline
Getting the 4-carbazole-nitrobenzene making in a certain amount of a and add in there-necked flask, is solvent at ethanol, does dropwise to add hydrazine hydrate under the condition of catalyst with palladium carbon, be warming up to 78-83 DEG C, stir 7 hours, cooling, suction filtration, revolves and steams except desolventizing, and vacuum drying obtains faint yellow solid.
The preparation of c, schiff bases micromolecular compound
Get the 4-carbazole aniline that step b makes and be dissolved in alcohol solvent, addN,N-ethyl diacetate benzaldehyde, carries out condensation,N,NThe mol ratio of-ethyl diacetate benzaldehyde and 4-carbazole-aniline is 1-1.5:1, and the 5-6h that refluxes at 70-75 DEG C, is cooled to room temperature, suction filtration, and with absolute ethanol washing, dry, obtain Compound I.
Schiff bases micromolecular compound synthetic route of the present invention is as follows:
According to the present invention, preferred, the ratio of the amount of substance of carbazole described in step a and p-fluoronitrobenzene is 1:4.
According to the present invention, preferred, carbazole described in step a and p-fluoronitrobenzene stir in nitrogen atmosphere, are heated to 150 DEG C, and reaction 12h has reacted rear and has been recrystallized with benzene.
According to the present invention, preferred, the carbazole-nitrobenzene of 4-described in step b and hydrazine hydrate reaction temperature are 80 DEG C.
According to the present invention, preferred, described in step cN,NThe mol ratio of-ethyl diacetate benzaldehyde and 4-carbazole-aniline is 1:1.
According to the present invention, preferred, described in step cN,NThe reaction time of-ethyl diacetate benzaldehyde and 4-carbazole-aniline is 6h.
According to the present invention, preferred, described in step cN,NThe reaction temperature of-ethyl diacetate benzaldehyde and 4-carbazole-aniline is 70 DEG C.
Brief description of the drawings
Fig. 1 is the nuclear-magnetism figure of the compounds of this invention I.
Fig. 2 is the infrared figure of the compounds of this invention I.
Detailed description of the invention
Below in conjunction with the drawings and specific embodiments, the present invention is described in detail, but be not limited to this. The little molecule of schiff bases, the foregoing formula I of molecular structural formula. Preparation method's step is as follows:
A, schiff bases are micromolecular synthetic: by 0.002mol'sN,N-ethyl diacetate benzaldehyde and 15mL absolute ethyl alcohol add in there-necked flask and are slowly warming up toN,N-ethyl diacetate benzaldehyde dissolves, and then adds 4-carbazole-aniline of 0.002mol to be warming up to 70 DEG C, stirs 6h, cooling, crystallize out, and suction filtration, and with absolute ethanol washing, dry, obtain the little molecule of novel schiff bases.1HNMR(CDCl3, 400Hz) and δ (ppm): 8.34 (s, 1H), 8.20-8.16 (m, 4H), 7.74-7.72 (s, 2H), 7.43-7.00 (m, 12H) 4.34 (s, 4H), 3.83 (s, 4H), 2.08 (s, 6H). according to Fig. 2 can find out the little molecule of schiff bases withN,N-Ethyl diacetate benzaldehyde is compared 1674cm-1The C=O of place vibration peak disappears, 3443cm compared with 4-carbazole-aniline-1And 3557cm-1The amino vibration peak at place disappears. Successfully synthesize in conjunction with Fig. 1 and Fig. 2 explanation the little molecule of novel schiff bases that foregoing molecular structural formula is I.
Claims (7)
1. the structure of a novel schiff bases Small-molecule probe is as follows
2. a preparation method for novel schiff bases Small-molecule probe compound described in claim 1, step is as follows:
Synthesizing of a, 4-carbazole-nitrobenzene
A certain amount of p-fluoronitrobenzene, carbazole, potash are added in there-necked flask, then add organic solvent DMF, under nitrogen protection, be warming up to 150-160 DEG C, stir 12h, be cooled to room temperature, reactant is poured in frozen water and washed, suction filtration, with benzene recrystallization, vacuum drying, obtains yellow crystals;
Synthesizing of b, 4-carbazole-aniline
Get the 4-carbazole-nitrobenzene making in a certain amount of a and add in there-necked flask, taking ethanol as solvent, do with palladium carbon dropwise to add hydrazine hydrate under the condition of catalyst, be warming up to 78-83 DEG C, stir 17 hours, cooling, suction filtration, revolves and steams desolventizing, and vacuum drying obtains faint yellow solid;
The preparation of c, schiff bases micromolecular compound
Get 4-carbazole-aniline that step b makes and be dissolved in alcohol solvent, add N, N-ethyl diacetate benzaldehyde carries out condensation, wherein N, the mol ratio of N-ethyl diacetate benzaldehyde and 4-carbazole-aniline is 1-1.5:1, the two 5-6h that refluxes at 75-77 DEG C, be cooled to room temperature, suction filtration, and with absolute ethanol washing, dry, obtain the little molecule I of schiff bases.
3. the preparation method of novel schiff bases micromolecular compound as claimed in claim 2, is characterized in that the fluoro-nitrobenzene of 4-described in a and carbazole amount of substance than being 4:1.
4. the preparation method of novel schiff bases micromolecular compound as claimed in claim 2, the reaction temperature that it is characterized in that p-fluoronitrobenzene described in a and carbazole is 153 DEG C, the reaction time is 12h.
5. the preparation method of novel schiff bases micromolecular compound as claimed in claim 2, the reaction temperature that it is characterized in that the carbazole-nitrobenzene of 4-described in b and hydrazine hydrate is 83 DEG C, the reaction time is 10h.
6. the preparation method of novel schiff bases micromolecular compound as claimed in claim 2, is characterized in that the carbazole-aniline of 4-described in c and N, and the ratio of the amount of substance of N-ethyl diacetate benzaldehyde is 1:1.
7. the preparation method of novel schiff bases micromolecular compound as claimed in claim 2, is characterized in that the carbazole-aniline of 4-described in c and N, and the reaction temperature of N-ethyl diacetate benzaldehyde is 70 DEG C, and the time is 5h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510667245.4A CN105585519A (en) | 2015-10-16 | 2015-10-16 | Preparation method of novel Schiff base micromolecular compound |
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| CN201510667245.4A CN105585519A (en) | 2015-10-16 | 2015-10-16 | Preparation method of novel Schiff base micromolecular compound |
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| CN201510667245.4A Pending CN105585519A (en) | 2015-10-16 | 2015-10-16 | Preparation method of novel Schiff base micromolecular compound |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0347967A1 (en) * | 1988-06-23 | 1989-12-27 | Agfa-Gevaert N.V. | Photosensitive recording material suited for use in electrophotography |
| CN104710344A (en) * | 2015-04-03 | 2015-06-17 | 齐鲁工业大学 | Schiff base type fluorescence probe compound taking carbazole as center and preparation thereof |
-
2015
- 2015-10-16 CN CN201510667245.4A patent/CN105585519A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0347967A1 (en) * | 1988-06-23 | 1989-12-27 | Agfa-Gevaert N.V. | Photosensitive recording material suited for use in electrophotography |
| CN104710344A (en) * | 2015-04-03 | 2015-06-17 | 齐鲁工业大学 | Schiff base type fluorescence probe compound taking carbazole as center and preparation thereof |
Non-Patent Citations (1)
| Title |
|---|
| 赵 琼等: ""新型偶氮化合物的合成及其光学性质"", 《合成化学》 * |
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Application publication date: 20160518 |
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