CN107759545A - A kind of method that one kettle way prepares N (5 methyl furfuryl group) P-nethoxyaniline - Google Patents
A kind of method that one kettle way prepares N (5 methyl furfuryl group) P-nethoxyaniline Download PDFInfo
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- CN107759545A CN107759545A CN201711076942.8A CN201711076942A CN107759545A CN 107759545 A CN107759545 A CN 107759545A CN 201711076942 A CN201711076942 A CN 201711076942A CN 107759545 A CN107759545 A CN 107759545A
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- nethoxyaniline
- methyl
- furfuryl group
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- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 title abstract description 33
- 238000000034 method Methods 0.000 title abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000003756 stirring Methods 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000012298 atmosphere Substances 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- OUDFNZMQXZILJD-UHFFFAOYSA-N 5-methyl-2-furaldehyde Chemical compound CC1=CC=C(C=O)O1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims 2
- HFFUVGRKJROWGR-UHFFFAOYSA-N 4-methoxy-n-[(5-methylfuran-2-yl)methyl]aniline Chemical compound C1=CC(OC)=CC=C1NCC1=CC=C(C)O1 HFFUVGRKJROWGR-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 2
- 238000011079 streamline operation Methods 0.000 abstract description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- -1 P-methoxyphenyl imines Chemical class 0.000 description 10
- 238000005576 amination reaction Methods 0.000 description 6
- 238000005485 electric heating Methods 0.000 description 6
- 239000013067 intermediate product Substances 0.000 description 6
- 238000005649 metathesis reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000010606 normalization Methods 0.000 description 6
- 230000001737 promoting effect Effects 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229960001669 kinetin Drugs 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A kind of preparation method of N (5 methyl furfuryl group) P-nethoxyaniline, comprises the following steps：Multiphase hydrogenation catalyst, 5 methyl furfurals, solvent, P-nethoxyaniline are added in reaction vessel successively, in the hydrogen atmosphere of normal pressure ~ 2.0Mpa pressure, under the reaction temperature of normal temperature ~ 100 DEG C, stirring, react 0.2 ~ 30h, separating catalyst and product.Streamline operation of the present invention, the loss of material that intermediate steps are brought is avoided, realize that resource maximally utilizes；Under suitable process conditions, the reaction time is substantially reduced, reduces production cost, improves production efficiency；Carry out in a mild condition, it is less demanding to production equipment, meet the principle of safety in production.
Description
Technical field
The invention belongs to compound synthesis method field.
Background technology
N- (5- methyl furfuryl group) P-nethoxyaniline（CAS 95124-39-3；C13H15NO2；2-Furanmethanamine,
N-(4-methoxyphenyl)-5-methyl-）With certain bacteria resistance function（Fedor I. Zubkov, Vladimir P.
Zaytsev, Eugeniya V. Nikitina, et al. Tetrahedron, 2011, 9148-9163）, generally by two
Prepared by footwork, that is, first pass through 5 methyl furfural and react to obtain the N- (5- methyl furfuryl group) containing carbon-to-nitrogen double bon with P-nethoxyaniline
P-methoxyphenyl imines, then C=N is reduced by hydroborating reagent and obtains target product N- (5- methyl furfuryl group) to methoxybenzene
Amine, wherein hydroborating reagent include (Zivko Klepo, the Kresimir Jakopcic. such as magnesium/Reduction of methanol system, sodium borohydride
J. Chem. Eng. Data, 1985, 235-237；Fernando D. Suvire, Maximiliano Sortino,
Vladimir V. Kouznetsov, et al. Enriz. Bioorgan. Med. Chem., 2006, 1851-1867；
Igor V. Trushkov,Tatyana A. Nevolina,Vitaly A. Shcherbinin, et al.
Tetrahedron Lett., 2013, 3974-3976).Although existing lot of documents shows the hydroborating reagent energy such as sodium borohydride
Enough successfully reduction C=N also can be easily by aldehyde into C-N, but simultaneously（Or ketone）Carbonyl reduction is into alcohol so that reduction amination process
It need to be carried out in two steps, and the waste of a large amount of expensive hydroborating reagents is caused using the hydroborating reagent of excess.Therefore 5- methyl is sought
The new route that furfural direct-reduction amination obtains N- (5- methyl furfuryl group) P-nethoxyaniline is imperative.In fact, by Pd,
The direct-reduction amination of the metal catalyzed hydrogenations such as Ni, Pt, have been used to industrially prepared (the Shigeo Nishimura. of several amine
Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis,
Wiley, New York, 2001).Wherein Pd/C is most common wide variety of hydro-reduction catalyst, for by C=O
Be formed as new amine compound with amine reduction.It is generally acknowledged that pilot process passes through imines, but it is not required to separate, continues to urge through Pd/C
Change C=N hydrogenations, generate required amine compound (George N. Karageorge, John E. Macor.
Tetrahedron Lett.,2011,5117-5119).But directly gone back with P-nethoxyaniline by being catalyzed 5 methyl furfural
The report that former amination obtains N- (5- methyl furfuryl group) P-nethoxyaniline is more rarely seen.
The content of the invention
The problems such as cost is high, technique is cumbersome, low yield is prepared to solve existing N- (5- methyl furfuryl group) P-nethoxyaniline,
The present invention is provided under a kind of atmosphere of hydrogen, adds heterogeneous catalyst, using simple one kettle way, by 5 methyl furfural and to methoxy
The method that the direct-reduction amination of base aniline prepares N- (5- methyl furfuryl group) P-nethoxyaniline.
The present invention have it is simple, efficiently, industrialization cost is low, is easy to the advantages of industrialization.So far, 5 methyl furfural
Reduction amination is directly catalyzed with P-nethoxyaniline and prepares the research of N- (5- methyl furfuryl group) P-nethoxyaniline foreign language at home
It is not reported in offering, the research is significant.
The purpose of the present invention is achieved through the following technical solutions.
A kind of preparation method of N- (5- methyl furfuryl group) P-nethoxyaniline of the present invention, comprises the following steps：Will
Multiphase hydrogenation catalyst, 5 methyl furfural, solvent, P-nethoxyaniline are added in reaction vessel successively, in normal pressure ~ 2.0Mpa pressures
The hydrogen atmosphere of power, under the reaction temperature of normal temperature ~ 100 DEG C, stirring, react 0.2 ~ 30h, separating catalyst and product.
Described multiphase hydrogenation catalyst is support type more than one or both of Ru, Rh, Pd, Pt, Fe or Ni etc.
Catalyst, it is reusable.
Described catalyst amount（Measured by active component）For 0.01 ~ 1 mol% of reaction substrate 5 methyl furfural.
In described reaction, the ratio between amount of material of reaction substrate 5 methyl furfural and P-nethoxyaniline is 1:0.5~1:
1.5。
Described solvent is selected from the conventional organic solvents such as ethanol, ethyl acetate, toluene or benzene；Solvent load is reaction substrate
5 ~ 50 times of cumulative volume.
Compared with prior art, its advantage is the present invention.
（1）The preparation of N- (5- methyl furfuryl group) P-nethoxyaniline of the present invention streamline operation, avoids through one pot of completion
The loss of material that intermediate steps are brought, realizes that resource maximally utilizes.
（2）The preparation of N- (5- methyl furfuryl group) P-nethoxyaniline of the present invention is through one pot of completion, in suitable process conditions
Under, the reaction time is substantially reduced, reduces production cost, improves production efficiency.
（3）The preparation of N- (5- methyl furfuryl group) P-nethoxyaniline of the present invention is carried out in a mild condition, to production equipment
It is less demanding, meet the principle of safety in production.
Brief description of the drawings
Fig. 1 is the gas-chromatography that reaction solution obtained by N- (5- methyl furfuryl group) P-nethoxyaniline process is prepared by embodiment 1
Figure.
Fig. 2 is the mass spectrogram that target product obtained by N- (5- methyl furfuryl group) P-nethoxyaniline process is prepared by embodiment 1.
Fig. 3 is the nuclear-magnetism hydrogen that target product obtained by N- (5- methyl furfuryl group) P-nethoxyaniline process is prepared by embodiment 1
Spectrogram.
Embodiment
With reference to embodiment, the present invention is described in further detail.
It will be understood to those of skill in the art that the following example is merely to illustrate the present invention, and it should not be regarded as limiting this hair
Bright scope.In the examples where no specific technique or condition is specified, according to the technology or condition described by document in the art
Or carried out according to product description.Agents useful for same or the unreceipted production firm person of instrument, it is that can be obtained by buying
Conventional products.
Embodiment 1.
In with magnetic stir bar autoclave, 10mg Pd/C, 500ul 5 methyl furfurals, 20ml are successively added
Ethyl acetate, 0.6783g P-nethoxyaniline, kettle is closed, and with the air in hydrogen metathesis reactor, and ensure to react initial hydrogen
Atmospheric pressure is 1.2Mpa, and autoclave is placed in electric heating cover, is warming up to 90 DEG C, stirring reaction 4h.React laggard promoting the circulation of qi
Analysis of hplc, calculated by area normalization method, substrate 5 methyl furfural, the conversion ratio of P-nethoxyaniline reach respectively
To 96.87%, 88.60%, intermediate product N- (5- methyl furfuryl group) p-methoxyphenyl imines and target product N- (5- first in system
Base furfuryl group) percentage composition of P-nethoxyaniline is respectively 31.04%, 55.10%.
Fig. 1 is the gas-chromatography that the present embodiment prepares reaction solution obtained by N- (5- methyl furfuryl group) P-nethoxyaniline process
Figure.As illustrated, retention time 10.289min corresponds to 5 methyl furfural, 21.233min corresponds to P-nethoxyaniline,
31.178min corresponds to N- (5- methyl furfuryl group) P-nethoxyaniline, and 31.886min corresponds to N- (5- methyl furfuryl group) to methoxybenzene
Base imines.
Fig. 2 is the mass spectrogram that the present embodiment prepares target product obtained by N- (5- methyl furfuryl group) P-nethoxyaniline process.
Fig. 3 is the nucleus magnetic hydrogen spectrum that the present embodiment prepares target product obtained by N- (5- methyl furfuryl group) P-nethoxyaniline process
Figure.
Embodiment 2.
In with magnetic stir bar autoclave, 15mg Pd/C, 500ul 5 methyl furfurals, 20ml are successively added
Ethyl acetate, 0.6781g P-nethoxyaniline, kettle is closed, and with the air in hydrogen metathesis reactor, and ensure to react initial hydrogen
Atmospheric pressure is 0.8Mpa, and autoclave is placed in electric heating cover, is warming up to 70 DEG C, stirring reaction 2h.React laggard promoting the circulation of qi
Analysis of hplc, calculated by area normalization method, substrate 5 methyl furfural, the conversion ratio of P-nethoxyaniline reach respectively
To 94.30%, 87.22%, intermediate product N- (5- methyl furfuryl group) p-methoxyphenyl imines and target product N- (5- first in system
Base furfuryl group) percentage composition of P-nethoxyaniline is respectively 26.70%, 97.10%.
Embodiment 3.
In with magnetic stir bar autoclave, 10mg Pd/C, 500ul 5 methyl furfurals, 20ml are successively added
Ethanol, 0.6779g P-nethoxyaniline, kettle is closed, and with the air in hydrogen metathesis reactor, and ensure to react initial hydrogen pressure
Power is 1.2Mpa, and autoclave is placed in electric heating cover, is warming up to 90 DEG C, stirring reaction 4h.React laggard promoting the circulation of qi phase color
Spectrum analysis, is calculated, substrate 5 methyl furfural, the conversion ratio of P-nethoxyaniline respectively reach by area normalization method
100%th, 91.60%, intermediate product N- (5- methyl furfuryl group) p-methoxyphenyl imines and target product N- (5- methyl chaffs in system
Base) percentage composition of P-nethoxyaniline is respectively 25.44%, 66.15%.
Embodiment 4.
In with magnetic stir bar autoclave, 15mg Pd/C, 500ul 5 methyl furfurals, 20ml are successively added
Ethanol, 0.6782g P-nethoxyaniline, kettle is closed, and with the air in hydrogen metathesis reactor, and ensure to react initial hydrogen pressure
Power is 0.8Mpa, and autoclave is placed in electric heating cover, is warming up to 90 DEG C, stirring reaction 4h.React laggard promoting the circulation of qi phase color
Spectrum analysis, is calculated, substrate 5 methyl furfural, the conversion ratio of P-nethoxyaniline respectively reach by area normalization method
100%th, 92.73%, intermediate product N- (5- methyl furfuryl group) p-methoxyphenyl imines and target product N- (5- methyl chaffs in system
Base) percentage composition of P-nethoxyaniline is respectively 4.13%, 88.60%.
Embodiment 5.
In with magnetic stir bar autoclave, 15mg Pd/C, 500ul 5 methyl furfurals, 20ml are successively added
Ethyl acetate, 0.6781g P-nethoxyaniline, kettle is closed, and with the air in hydrogen metathesis reactor, and ensure to react initial hydrogen
Atmospheric pressure is 1.2Mpa, and autoclave is placed in electric heating cover, is warming up to 70 DEG C, stirring reaction 4h.React laggard promoting the circulation of qi
Analysis of hplc, calculated by area normalization method, substrate 5 methyl furfural, the conversion ratio of P-nethoxyaniline reach respectively
To 98.52%, 92.12%, intermediate product N- (5- methyl furfuryl group) p-methoxyphenyl imines and target product N- (5- first in system
Base furfuryl group) percentage composition of P-nethoxyaniline is respectively 1.42%, 89.44%.
Embodiment 6.
In with magnetic stir bar autoclave, 15mg Pd/C, 500ul 5 methyl furfurals, 20ml are successively added
Ethyl acetate, 0.6773g P-nethoxyaniline, kettle is closed, and with the air in hydrogen metathesis reactor, and ensure to react initial hydrogen
Atmospheric pressure is 1.2Mpa, and autoclave is placed in electric heating cover, is warming up to 90 DEG C, stirring reaction 4h.React laggard promoting the circulation of qi
Analysis of hplc, calculated by area normalization method, substrate 5 methyl furfural, the conversion ratio of P-nethoxyaniline reach respectively
To 99.08%, 92.63%, intermediate product N- (5- methyl furfuryl group) p-methoxyphenyl imines and target product N- (5- first in system
Base furfuryl group) percentage composition of P-nethoxyaniline is respectively 1.60%, 90.24%.
General principle, principal character and the advantages of the present invention of the present invention has been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the simply explanation described in above-described embodiment and specification is originally
The principle of invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention is by appended claim and its waits
Effect thing defines.
Claims (1)
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003038109A2 (en) * | 2001-09-18 | 2003-05-08 | The Board Of Regents Of The University Of Nebraska | Method for the inhibition of methanogenesis |
| CN107001312A (en) * | 2014-12-15 | 2017-08-01 | 有机燃料瑞典公司 | Synthesis of amides and amines from aldehydes or ketones via heterogeneous metal catalysis |
-
2017
- 2017-11-06 CN CN201711076942.8A patent/CN107759545A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003038109A2 (en) * | 2001-09-18 | 2003-05-08 | The Board Of Regents Of The University Of Nebraska | Method for the inhibition of methanogenesis |
| CN107001312A (en) * | 2014-12-15 | 2017-08-01 | 有机燃料瑞典公司 | Synthesis of amides and amines from aldehydes or ketones via heterogeneous metal catalysis |
Non-Patent Citations (2)
| Title |
|---|
| IGOR V. TRUSHKOV ET AL.: ""Furan ring opening-pyrrole ring closure. A simple route to 1,2,3,4-tetrahydropyrrolo[1,2-α]pyrazin-3-ones"", 《TETRAHEDRON LETTERS》 * |
| L. HIZARTZIDIS ET AL.: ""Chemoselective flow hydrogenation approaches to isoindole-7-carboxylic acids and 7-oxa-bicyclio [2.2.1]heptanes"", 《RSC ADVANCES》 * |
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