CN107513078A - A kind of preparation method of 2,6 diamino-pyridine contracting, 3 carboxyl benzaldehyde bis-Schiff base cobalt complexes - Google Patents
A kind of preparation method of 2,6 diamino-pyridine contracting, 3 carboxyl benzaldehyde bis-Schiff base cobalt complexes Download PDFInfo
- Publication number
- CN107513078A CN107513078A CN201710837109.4A CN201710837109A CN107513078A CN 107513078 A CN107513078 A CN 107513078A CN 201710837109 A CN201710837109 A CN 201710837109A CN 107513078 A CN107513078 A CN 107513078A
- Authority
- CN
- China
- Prior art keywords
- contracting
- carboxyl
- diamino
- bis
- carboxyl benzaldehyde
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002262 Schiff base Substances 0.000 title claims abstract description 45
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 title abstract 5
- 238000000034 method Methods 0.000 claims abstract description 33
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 229940011182 cobalt acetate Drugs 0.000 claims abstract description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 27
- UHDNUPHSDMOGCR-UHFFFAOYSA-N 3-Formylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=O)=C1 UHDNUPHSDMOGCR-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000001556 precipitation Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000012153 distilled water Substances 0.000 claims description 10
- 235000019441 ethanol Nutrition 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000013019 agitation Methods 0.000 claims description 6
- 238000010009 beating Methods 0.000 claims description 6
- 125000005909 ethyl alcohol group Chemical group 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims 2
- 239000013049 sediment Substances 0.000 claims 1
- 238000005303 weighing Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 2
- IKRFKSWGOJLRBP-UHFFFAOYSA-N C(=O)(O)C=1C=C(C=O)C=CC1.NC1=NC(=CC=C1)N Chemical compound C(=O)(O)C=1C=C(C=O)C=CC1.NC1=NC(=CC=C1)N IKRFKSWGOJLRBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 9
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- -1 schiff bases cobalt complex Chemical class 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001027 hydrothermal synthesis Methods 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000005935 nucleophilic addition reaction Methods 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000005287 template synthesis Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910020676 Co—N Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- 229910001429 cobalt ion Inorganic materials 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention discloses a kind of preparation method of 2,6 diamino-pyridine 3 carboxyl benzaldehyde bis-Schiff base cobalt complexes of contracting.With 2,6 diamino-pyridines and 3 carboxyl benzaldehydes are raw material, using absolute ethyl alcohol as solvent, it is not necessary to add catalyst, prepare 2,6 diamino-pyridines, 3 carboxyl benzaldehyde bis-Schiff bases of contracting, then 3 carboxyl benzaldehyde bis-Schiff bases are contracted for part with 2,6 diamino-pyridines, in alkaline aqueous solution, reacted with cobalt acetate, prepare 2,6 diamino-pyridines, 3 carboxyl benzaldehyde bis-Schiff base cobalt complexes of contracting.The inventive method need not add catalyst, have the advantages of simple technique, reproducible, high yield, easy to utilize.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of DAP contracting 3- carboxyl benzaldehydes are double
The preparation method of schiff bases cobalt complex.
Background technology
Schiff bases are that have imino group by what active aminated compounds and carbonyl complex generated after condensation reaction
A kind of compound of (- C=N-) or imino group (- RC=N-) structure.N atoms contain lone pair electrons in such compound C=N keys, because
This such compound has good coordination activity.The species of schiff bases is various, and synthetic method is simple, and researcher can be flexible
Selection amine and the aldehydes or ketones containing carbonyl are reacted to obtain schiff bases, while the substituted radical of also controllable schiff bases and are matched somebody with somebody
Position environment, metal complex is formed with Determination of multiple metal elements.
The synthesis of schiff bases is a reaction for being related to nucleophilic addition, i.e., by be used as the aminated compounds of nucleopilic reagent with
Carbonyl complex forms schiff bases by the reaction such as addition, cancellation, rearrangement, dehydration.
Schiff bases and its synthetic method of complex mainly have direct synthesis technique, distribution synthetic method, template synthesis method, dropwise
Reaction method, hydrothermal synthesis method etc..
Direct synthesis technique is called live synthetic method.The method is relatively easy, i.e., under given conditions by carbonyl class chemical combination
Thing, aminated compounds or amino acid can obtain metal complex with metal ion by certain mixed in molar ratio reaction.It is this
The advantages of method is that reaction is fast, yield is high, easy to operate simple；Shortcoming is that side reaction occurs and is unfavorable for purification and the table of product
Sign.
Step synthesis are carried out in two steps.The first step, under certain condition, aminated compounds are carried out with carbonyl complex
Nucleophilic addition, product is carried out to be recrystallized to give schiff base compound；Second step, the schiff bases chemical combination after the first step is recrystallized
Thing is reacted according to a certain percentage with metal salt, you can obtains Schiff base metal complexes.Thus the product that method obtains is pure
And yield is higher.
Template synthesis method use can be added in carbonyls as the metal ion of " template ", then again and amine
Class compound is reacted.Wherein " template " can promote organic ligand and the generation of small organic molecule orientation generation bigger molecule
Organic coordination compound.The method has that high selectivity, high yield, reaction speed be fast, simple operation and other advantages.
When schiff bases easily separate out and during indissoluble, above several method it is inapplicable, at this moment can uses reaction method dropwise.
First primary amine compound is mixed with metal ion solution, aldehyde, ketone carbonyl containing compound is then added dropwise, is stirred vigorously
Under, there are micro schiff bases to obtain presence of Schiff-base complex with the reaction of a large amount of metal ions immediately when generating.
Hydrothermal synthesis method is put into Schiff base ligand, metal salt and molten i.e. in the autoclave of polytetrafluoroethylene (PTFE) bottle
Agent, then reactor is placed in the baking oven with certain temperature, reactant is mixed under high pressure and high temperature condition with solvent
React, after cooling decompression, purer crystal is separated out from solvent middle reaches.
Schiff bases and its metal complex have good antitumor, antibacterial, anti-oxidant, antiviral isoreactivity, in chemistry
The fields such as catalysis, biological medicine, functional material, food industry have a good application prospect, and are also played in electrochemical field
Important effect.Therefore, continually develop and prepare new schiff bases and its metal complex, have very strong scientific research value and
Practical application potentiality.
The invention discloses the preparation side of 2,6- diamino-pyridine contracting 3- carboxyl benzaldehydes bis-Schiff bases and its cobalt complex
Method.Methods described is using DAP and 3- carboxyl benzaldehydes as raw material, it is not necessary to adds catalyst, you can prepares 2,6-
Diamino-pyridine contracting 3- carboxyl benzaldehyde bis-Schiff bases, then using DAP contracting 3- carboxyl benzaldehydes bis-Schiff base as with
Body, reacted with cobalt acetate, prepare DAP contracting 3- carboxyl benzaldehyde bis-Schiff base cobalt complexes.The present invention's is described
Method has the advantages that being not required to add catalyst, technique is simple, reproducible, yield is high.
The content of the invention
It is an object of the invention to provide a kind of 2,6- diamino-pyridines contracting 3- carboxyl benzaldehyde bis-Schiff base cobalt complexes
Preparation method.
Concretely comprise the following steps：
（1）Weigh 0.6000 g（4 mmol）3- carboxyl benzaldehydes are dissolved in 10 mL absolute ethyl alcohols, and magnetic agitation is uniform, obtains
Water white transparency settled solution.
（2）By 0.2180 g（2 mmol）DAP is dissolved in 5 mL absolute ethyl alcohols, then by step（1）System
The water white transparency settled solution obtained is slowly dropped into, nitrogen protection, carries out back flow reaction 4 hours under the conditions of 65 DEG C, has precipitation to generate,
Stand, cool down, filter, must precipitate.
（3）By step（2）The precipitation of middle acquisition, successively purified using beating method, recrystallization method, after vacuum drying,
Buff powder, as DAP contracting 3- carboxyl benzaldehyde bis-Schiff bases is made；The solvent of the beating method is nothing
Water-ethanol, the recrystallization method are 1 using volume ratio:1 dimethyl sulfoxide (DMSO)（DMSO）With absolute ethyl alcohol mixed solvent.
（4）It is 1 in molar ratio:1:2 weigh 0.3730 g (1 mmol) step respectively（3）Obtained 2,6- diaminourea pyrrole
Pyridine contracting 3- carboxyl benzaldehydes bis-Schiff base, 0.2492 g (1 mmol) cobalt acetates and 0.0800 g (2 mmol) hydroxide
Sodium.
（5）First will（4）In the 2,6- diamino-pyridine contracting 3- carboxyl benzaldehyde bis-Schiff bases that weigh be dissolved in 10 mL distillations
In water, turbid solution is made, by step（4）In the sodium hydroxide that weighs be dissolved in 5 mL distilled water, it is while stirring that its is slow
It is added dropwise in obtained turbid solution, turbid solution gradually becomes settled solution.
（6）Again by step（4）In the cobalt acetate that weighs be dissolved in 5 mL distilled water, be then slowly dropped to step
（5）In obtained settled solution, back flow reaction 12 hours under conditions of magnetic agitation, 65 DEG C, there is blackish green precipitation generation,
After suction filtration, the precipitation is washed 3 times with DMSO, each DMSO dosage is 10 mL, then with the distillation water washing precipitation 3
Secondary, the dosage of each distilled water is 10 mL, after vacuum drying, obtains yellow greenish powder, as DAP contracting 3- carboxylics
Benzaldehyde bis-Schiff base cobalt complex.
The inventive method need not add catalyst, have the advantages of simple technique, reproducible, high yield, be easy to promote
Using.
Brief description of the drawings
Fig. 1 is the red of obtained 2,6- diamino-pyridines contracting 3- carboxyl benzaldehyde bis-Schiff base matter in the embodiment of the present invention
External spectrum figure.
Fig. 2 is that obtained 2,6- diamino-pyridines contracting 3- carboxyl benzaldehyde bis-Schiff bases cobalt coordinates in the embodiment of the present invention
The infrared spectrogram of thing.
Embodiment
Embodiment：
With reference to specific embodiment, the present invention is furture elucidated, but embodiment is not intended to limit protection scope of the present invention.
（1）Weigh 0.6000 g（4 mmol）3- carboxyl benzaldehydes are dissolved in 10 mL absolute ethyl alcohols, and magnetic agitation is uniform,
Obtain water white transparency settled solution.
（2）By 0.2180 g（2 mmol）DAP is dissolved in 5 mL absolute ethyl alcohols, then by step（1）System
The water white transparency settled solution obtained is slowly dropped into, nitrogen protection, carries out back flow reaction 4 hours under the conditions of 65 DEG C, has precipitation to generate,
Stand, cool down, filter, must precipitate.
（3）By step（2）The precipitation of middle acquisition, successively purified using beating method, recrystallization method, after vacuum drying,
Buff powder is made, as DAP contracting 3- carboxyl benzaldehyde bis-Schiff bases, yield 77.8%, fusing point is
282.8-284.6℃；The solvent of the beating method is absolute ethyl alcohol, and the recrystallization method is 1 using volume ratio:1 dimethyl
Sulfoxide（DMSO）With absolute ethyl alcohol mixed solvent.
（4）It is 1 in molar ratio:1:2 weigh 0.3730 g (1 mmol) step respectively（3）Obtained 2,6- diaminourea pyrrole
Pyridine contracting 3- carboxyl benzaldehydes bis-Schiff base, 0.2492 g (1 mmol) cobalt acetates and 0.0800 g (2 mmol) hydroxide
Sodium.
（5）First will（4）In the 2,6- diamino-pyridine contracting 3- carboxyl benzaldehyde bis-Schiff bases that weigh be dissolved in 10 mL distillations
In water, turbid solution is made, by step（4）In the sodium hydroxide that weighs be dissolved in 5 mL distilled water, it is while stirring that its is slow
It is added dropwise in obtained turbid solution, turbid solution gradually becomes settled solution.
（6）Again by step（4）In the cobalt acetate that weighs be dissolved in 5 mL distilled water, be then slowly dropped to step
（5）In obtained settled solution, back flow reaction 12 hours under conditions of magnetic agitation, 65 DEG C, there is blackish green precipitation generation,
After suction filtration, the precipitation is washed 3 times with DMSO, each DMSO dosage is 10 mL, then with the distillation water washing precipitation 3
Secondary, the dosage of each distilled water is 10 mL, after vacuum drying, obtains yellow greenish powder, as DAP contracting 3- carboxylics
Benzaldehyde bis-Schiff base cobalt complex, yield 73.62%, fusing point are 299.7-304.1 DEG C.
Infrared spectrum analysis (the accompanying drawing of 2,6- diamino-pyridines contracting 3- carboxyl benzaldehyde bis-Schiff bases made from the present embodiment
1)：In 3390-3170 cm-1Do not occur stretching vibration absworption peak in position range, illustrate-NH is not present2Stretching vibration inhale
Receive peak.1750-1710 cm-1In the range of there is not stretching vibration absworption peak, illustrate-CHO, 1647 cm is not present-1It is C=N
Stretching vibration absworption peak, this shows the generation for having schiff bases structure.1252 cm-1Carboxyl C-O stretching vibration absworption peaks, 930
cm-1It is O-H out-of-plane deformations vibration absorption peak in carboxyl, 757 cm-1It is the C-H out-of-plane deformation absorption of vibrations of phenyl ring meta substitution
Peak.The infrared spectrum analysis (accompanying drawing 2) of 2,6- diamino-pyridine contracting 3- carboxyl benzaldehyde bis-Schiff base cobalt complexes：C=N's stretches
Contracting vibration absorption peak moves to 1610 cm-1, this shows that C=N take part in the coordination of metal cobalt ions, in 520-700 cm-1Occur
New absworption peak, Co-N stretching vibration absworption peak can be attributed to.1422-1458 cm-1There is new absworption peak, can be attributed to
The characteristic absorption peak of acetate in complex.
Claims (1)
- A kind of 1. preparation method of DAP contracting 3- carboxyl benzaldehyde bis-Schiff base cobalt complexes, it is characterised in that tool Body step is：（1）The 3- carboxyl benzaldehydes for weighing 4 mmol are dissolved in 10 mL absolute ethyl alcohols, and magnetic agitation is uniform, obtains water white transparency Settled solution；（2）2 mmol DAP is dissolved in 5 mL absolute ethyl alcohols, then by step（1）Obtained water white transparency Settled solution is slowly dropped into, nitrogen protection, carries out back flow reaction 4 hours under the conditions of 65 DEG C, has precipitation to generate, stand, cool down, take out Filter, must be precipitated；（3）By step（2）The precipitation of middle acquisition, successively purified using beating method, recrystallization method, after vacuum drying, be made Buff powder, as DAP contracting 3- carboxyl benzaldehyde bis-Schiff bases；The solvent of the beating method is anhydrous second Alcohol, the recrystallization method are 1 using volume ratio:1 dimethyl sulfoxide (DMSO) and absolute ethyl alcohol mixed solvent；（4）It is 1 in molar ratio:1:2 weigh 1 mmol steps respectively（3）Obtained 2,6- diamino-pyridines contracting 3- carboxyl benzaldehydes Bis-Schiff base, 1 mmol cobalt acetates and 2 mmol sodium hydroxides；（5）First will（4）In the DAP contracting 3- carboxyl benzaldehyde bis-Schiff bases that weigh be dissolved in 10 mL distilled water, Turbid solution is made, by step（4）In the sodium hydroxide that weighs be dissolved in 5 mL distilled water, be slowly added dropwise while stirring into In obtained turbid solution, turbid solution gradually becomes settled solution；（6）Again by step（4）In the cobalt acetate that weighs be dissolved in 5 mL distilled water, be then slowly dropped to step（5）System In the settled solution obtained, back flow reaction 12 hours under conditions of magnetic agitation, 65 DEG C, there is blackish green precipitation generation, filter Afterwards, the precipitation is washed 3 times with dimethyl sulfoxide (DMSO), the dosage of each dimethyl sulfoxide (DMSO) is 10 mL, then this is heavy with distillation water washing Form sediment 3 times, the dosage of each distilled water is 10 mL, after vacuum drying, obtains yellow greenish powder, as DAP contracts 3- carboxyl benzaldehyde bis-Schiff base cobalt complexes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710837109.4A CN107513078B (en) | 2017-09-17 | 2017-09-17 | Preparation method of 2, 6-diaminopyridine condensed 3-carboxybenzaldehyde bis-Schiff base cobalt complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710837109.4A CN107513078B (en) | 2017-09-17 | 2017-09-17 | Preparation method of 2, 6-diaminopyridine condensed 3-carboxybenzaldehyde bis-Schiff base cobalt complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107513078A true CN107513078A (en) | 2017-12-26 |
| CN107513078B CN107513078B (en) | 2020-01-21 |
Family
ID=60725472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710837109.4A Active CN107513078B (en) | 2017-09-17 | 2017-09-17 | Preparation method of 2, 6-diaminopyridine condensed 3-carboxybenzaldehyde bis-Schiff base cobalt complex |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107513078B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997204A (en) * | 2018-09-06 | 2018-12-14 | 桂林理工大学 | A kind of preparation method of 2,6- diamino-pyridine contracting cinnamic acid Bis-Schiff Bases corrosion inhibiter |
-
2017
- 2017-09-17 CN CN201710837109.4A patent/CN107513078B/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997204A (en) * | 2018-09-06 | 2018-12-14 | 桂林理工大学 | A kind of preparation method of 2,6- diamino-pyridine contracting cinnamic acid Bis-Schiff Bases corrosion inhibiter |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107513078B (en) | 2020-01-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103880892B (en) | Acyl Ferrocene contracting S-methyldi-thiocarbazate Schiff and preparation method thereof | |
| Maurya et al. | Oxidation of secondary alcohols by conventional and microwave-assisted methods using molybdenum complexes of ONO donor ligands | |
| Zhang et al. | Synthesis of heteroaromatic trifluoromethyl ethers with trifluoromethyl triflate as the source of the trifluoromethoxy group | |
| CN102197014A (en) | Manufacture of gamma-delta-unsaturated ketones | |
| CN101817713A (en) | Preparation method of 2, 2'-biphenyl diphenol and derivatives thereof | |
| CN107501338A (en) | A kind of preparation method of 2,6 diamino-pyridine contracting, 4 carboxyl benzaldehyde bis-Schiff base cobalt complexes | |
| CN107513078A (en) | A kind of preparation method of 2,6 diamino-pyridine contracting, 3 carboxyl benzaldehyde bis-Schiff base cobalt complexes | |
| Paul et al. | Zn (II)-to-Cu (II) Transmetalation in an Amide Functionalized Complex and Catalytic Applications in Styrene Oxidation and Nitroaldol Coupling | |
| CN107513079A (en) | A kind of preparation method of 2,6 diamino-pyridine contracting 2-carboxybenzaldehyde bis-Schiff base cobalt complex | |
| CN101955480A (en) | Pyrazolo [3,4-b] quinoline compound and preparation method thereof | |
| JP6028606B2 (en) | Method for producing amine compound | |
| CN109535120A (en) | The preparation method of 7- substitution -3,4,4,7- tetrahydro cyclobutane and cumarin -5- ketone | |
| CN106622375B (en) | A kind of 2,4- 4-dihydroxy benzaldehyde contracting amino acid Raney nickel, preparation method and application | |
| TWI244473B (en) | A process for producing 1,2-diols by the reaction of olefins with hydroperoxide | |
| CN110759861B (en) | Preparation method of quinoline derivative | |
| KR20180073886A (en) | The preparation method of 4’-formyl-4-biphenylcarboxylic acid | |
| CN111470539A (en) | Preparation method of high-efficiency catalytic benzylamine oxidative coupling catalyst | |
| CN104876940A (en) | Synthesis method of hexatomic ring of aromatic foldamer | |
| RU2613976C1 (en) | Method for production of lanthanum organometallic frame compound of three-dimensional structures based on terephthalic acid | |
| CN109467523A (en) | A kind of green synthesis method of the third sulfonic acid chloride of 3- chlorine | |
| CN105268422B (en) | The preparation method of isophorone catalyst | |
| SE406461B (en) | METHOD OF PREPARING CYCLOHEXANONE OR CYCLOHEXANOL BY CONVERSION OF CYCLOHEXYL HYDROPEROXIDE USING A SOLID HETEROGENIC CHROMOXIDE CATALYST | |
| CN110642689B (en) | 3, 6-dibromo-2-methylbenzaldehyde and chemical synthesis method thereof | |
| Musalova et al. | Synthesis of divinyl ditelluride from tellurium and acetylene | |
| CN105753804A (en) | Method of preparing 3-morpholinone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20171226 Assignee: Guilin Hongshengda Chemical Reagent Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2022450000159 Denomination of invention: Preparation of a cobalt complex of 2,6-diaminopyridine 3-carboxybenzaldehyde bis Schiff base Granted publication date: 20200121 License type: Common License Record date: 20221124 |
|
| EE01 | Entry into force of recordation of patent licensing contract |