CN109053460A - A method of catalysis benzalcohol derivatives amination - Google Patents
A method of catalysis benzalcohol derivatives amination Download PDFInfo
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- CN109053460A CN109053460A CN201810803944.0A CN201810803944A CN109053460A CN 109053460 A CN109053460 A CN 109053460A CN 201810803944 A CN201810803944 A CN 201810803944A CN 109053460 A CN109053460 A CN 109053460A
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- benzalcohol derivatives
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- benzalcohol
- derivatives
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000005576 amination reaction Methods 0.000 title claims abstract description 7
- 238000006555 catalytic reaction Methods 0.000 title abstract description 6
- -1 amine compound Chemical class 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- QXALIERKYGCHHA-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)borane Chemical compound BC1=C(F)C(F)=C(F)C(F)=C1F QXALIERKYGCHHA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001448 anilines Chemical class 0.000 claims abstract description 7
- 229960004217 benzyl alcohol Drugs 0.000 claims abstract description 7
- 235000019445 benzyl alcohol Nutrition 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 claims description 3
- NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 claims description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 32
- 239000000126 substance Substances 0.000 abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 238000011109 contamination Methods 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012675 alcoholic extract Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to organic synthesis fields, disclose a kind of method for being catalyzed benzalcohol derivatives amination, benzalcohol derivatives are mixed with amino benzenes compounds, solvent and three pentafluorophenyl borane of catalyst is added, is reacted at 85 DEG C~120 DEG C 12-24 hours and obtains benzylalcohol aminate.The reaction realizes Catalysis for a series of benzalcohol derivatives using commercially available three pentafluorophenyl borane as catalyst; reaction is without carrying out pre-activate or protection to alcohol; it improves Atom economy and reduces chemical contamination, this method can efficiently construct a series of organic amine compound of different substituents.
Description
Technical field
The present invention is a kind of organic compound synthetic method, and in particular to be to be urged using nonmetallic lewis acid catalyst
Change alcohol compound aminating reaction, and is used the synthesis of series of different aminated compounds.
Background technique
Alcohol compound not only has extensive source and has low toxicity steady as a kind of important organic compound
The features such as determining has consequence in industry, medicine and fine chemistry industry.Nitrogen atom is synthesized by alcohol compound
Closing object is a kind of important chemical conversion, but since alcoholic extract hydroxyl group itself has the chemical property for being difficult to leave away, common
Need to carry out alcoholic extract hydroxyl group pre-activate or protection in chemical conversion mostly to reinforce its performance of leaving away, and in this course
Unnecessary atom waste and chemical contamination can then be generated.Currently, Green Chemistry and Atom economy are two big in chemical production
Important index.In conclusion the alcohol compound aminating reaction for developing a kind of green high-efficient is necessary and is of great significance
's.
The direct aminatin reaction that alcohol compound is realized using chemical catalysis method is that one kind is quickly obtained aminated compounds
Important method.The direct aminatin using metal Lewis acids Au catalyst for benzylalcohol is reported in Prim seminar in 2006
Reaction, catalyst used in the reaction are gold trichloride sodium chloride, use methylene chloride as solvent can to it is a series of not
Sulfonamide reaction is carried out with the benzylalcohol replaced.And must then it use sulfonamide etc. that there is weakly acidic amine source in this reaction
(formula 1).
Then develop in Chinese Scientists professor Xia Chungu in 2012 a kind of straight using azochlorosulfonate acid ion liquid catalyst benzylalcohol
Aminating reaction is connect, which can obtain benzhydrol sulfuryl amine product under being 80 degrees Celsius of solvent in Isosorbide-5-Nitrae-dioxane
(formula 2).
At present it has been reported that alcohol compound direct aminatin reaction in, be typically necessary using metal Lewis acids,
And amine source is necessary for sulfonamide, and amide etc. is a series of to have weakly acidic organic amine, and these restrictive conditions are not able to satisfy
Practical application in Chemical Manufacture, therefore it is anti-to develop the alcohol amination that a kind of nonmetal catalyzed and amine source is aromatic amine compounds
It should be necessary.
Summary of the invention
Benzalcohol derivatives direct aminatin is catalyzed using three pentafluorophenyl boranes the purpose of the present invention is to provide a kind of
Method.
The purpose of the present invention is achieved through the following technical solutions:
A method of benzalcohol derivatives are mixed with amino benzenes compounds, are added by catalysis benzalcohol derivatives amination
Solvent and three pentafluorophenyl borane of catalyst, it is to obtain benzylalcohol aminate that 12-24 hours reacts at 85 DEG C~120 DEG C.
This method is specific as follows:
The benzalcohol derivatives areWherein R1 group is hydrogen atom, alkyl, aryl, ester group, halogen
Element；R2 group is alkyl, aryl or cyano.
Preferably, the benzalcohol derivatives are benzhydrol and the like, benzyl carbinol and the like (1- phenyl second
Alcohol) or benzaldehyde cyanohydrin.
The amino benzenes compounds areR3 group is methoxyl group, alkyl or aryl.
Preferably, the amino benzenes compounds are P-nethoxyaniline or open-chain crown ether.
Preferably, the molar ratio of the benzalcohol derivatives and aromatic amine compounds is 1:2.
Preferably, the additive amount of the catalyst is 1%-20%.
Preferably, the additive amount molar percentage of the catalyst is 1%-20%.
Preferably, the molar ratio of the benzalcohol derivatives and catalyst is 1:0.1.
Preferably, the solvent is nitromethane, toluene, 1,2- dichloroethanes, tetrahydrofuran or chloroform.
Compared with prior art, the present invention has the advantage that
(1) present invention is catalyzed using three pentafluorophenyl boranes for benzylalcohol types of substrates aminating reaction.The reaction utilizes quotient
Available three pentafluorophenyl borane of industry as catalyst for a series of benzalcohol derivatives realize Catalysis, reaction without pair
Alcohol, which carries out pre-activate or protection, this method, can efficiently construct a series of organic amine compound of different substituents.
(2) operation of the present invention is simple, and reaction is efficient and will not generate extra chemical contamination, and atom utilization is high.
Detailed description of the invention
Fig. 1 is the nuclear magnetic resonance figures that product is made in embodiment 1, and (a) is hydrogen spectrogram, (b) is carbon spectrogram.
Fig. 2 is the nuclear magnetic resonance figures that product is made in embodiment 2, and (a) is hydrogen spectrogram, (b) is carbon spectrogram.
Fig. 3 is the nuclear magnetic resonance figures that product is made in embodiment 3, and (a) is hydrogen spectrogram, (b) is carbon spectrogram.
Fig. 4 is the nuclear magnetic resonance figures that product is made in embodiment 4, and (a) is hydrogen spectrogram, (b) is carbon spectrogram.
Specific embodiment
The present invention is further explained in the light of specific embodiments.
Embodiment 1
Benzhydrol (36.8mg) is placed in 10 milliliters of reaction tubes, 1 milliliter of nitromethane is added as solvent, then adds
Enter tri- pentafluorophenyl borane of 11mg and P-nethoxyaniline (49.2mg), reaction temperature is increased to 120 degrees Celsius, reacts 12 hours
Product is separated by column chromatography after afterwards then removing solvent the reaction is cooled to room temperature: N- benzhydryl -4- first
Oxygroup aniline (49mg, yield 86%) brown liquid, 86% yield.Analyze data:1H NMR(400MHz,CDCl3)δ7.34(m,
8H), 7.27-7.22 (m, 2H), 6.71 (d, J=8.9Hz, 2H), 6.50 (d, J=8.9Hz, 2H), 5.41 (s, 1H), 3.70
(s,3H).13C NMR(100MHz,CDCl3)δ152.14,143.22,141.70,128.74,127.42,127.31,114.74,
114.63,63.84,55.75.HRMS(ESI)m/z[M+H]+:Calcd for C20H20NO:290.1545.Found:
290.1524.
Embodiment 2
1- phenylethanol (24.4mg) is placed in 10 milliliters of reaction tubes, 1 milliliter of nitromethane is added as solvent, then
Tri- pentafluorophenyl borane of 11mg and P-nethoxyaniline (49.2mg) is added, reaction temperature is increased to 120 degrees Celsius, and reaction 12 is small
When after then solvent is removed the reaction is cooled to room temperature after by column chromatography product is separated: 4- methoxyl group-N- (1-
Phenethyl) aniline (30mg, yield 67%) colourless liquid, 67% yield.Analyze data:1H NMR(400MHz,CDCl3)δ
7.33 (dt, J=13.1,7.4Hz, 4H), 7.21 (t, J=7.8Hz, 1H), 6.68 (d, J=8.9Hz, 2H), 6.46 (d, J=
8.9Hz, 2H), 4.40 (q, J=6.7Hz, 1H), 3.68 (s, 3H), 1.49 (d, J=6.7Hz, 3H) .13C NMR (100MHz,
CDCl3)δ151.89,145.51,141.58,128.64,126.84,125.91,114.77,114.55,55.75,54.27,
25.17.HRMS(ESI)m/z[M+H]+:Calcd for C15H18NO:228.1388.Found:228.1370.
Embodiment 3
Benzaldehyde cyanohydrin (26.6mg) is placed in 10 milliliters of reaction tubes, 1 milliliter of nitromethane is added as solvent, is then added
Tri- pentafluorophenyl borane of 11mg and P-nethoxyaniline (49.2mg), after reaction temperature is increased to 120 degrees Celsius, reaction 12 hours
Product is separated by column chromatography after then removing solvent the reaction is cooled to room temperature: 2- (4- methoxyphenyl)
Amine -2- phenylacetonitrile (33mg, yield 68%) colourless liquid, 68% yield.Analyze data:1H NMR(400MHz,CDCl3)δ
7.66-7.56 (m, 2H), 7.45 (dt, J=11.9,4.1Hz, 3H), 6.85 (d, J=8.9Hz, 2H), 6.76 (d, J=
6.7Hz, 2H), 5.34 (d, J=8.4Hz, 1H), 3.77 (s, 3H)13C NMR(100MHz,CDCl3)δ154.16,138.59,
134.16,129.47,129.29,127.28,118.48,116.34,115.02,55.68,51.61.HRMS(ESI)m/z[M+
H]+:Calcd for C15H15N2O:239.1184.Found:239.1165.
Embodiment 4
2- hydroxyl -2- Phenyl ethyl ketone (42.4mg) is placed in 10 milliliters of reaction tubes, 1 milliliter of nitromethane is added as molten
Agent is then added tri- pentafluorophenyl borane of 11mg and P-nethoxyaniline (49.2mg), reaction temperature is increased to 120 degrees Celsius,
Reaction separates product by column chromatography after then removing solvent the reaction is cooled to room temperature after 12 hours: 2- (4-
Methoxyphenyl) imines -1,2- tolans -1- ketone (51.2mg, yield 81%).Colourless liquid, 81% yield.Analyze number
According to:1H NMR(400MHz,CDCl3) δ 7.86 (d, J=7.9Hz, 2H), 7.77 (d, J=7.9Hz, 2H), 7.44 (dt, J=
21.7,7.5Hz, 4H), 7.33 (t, J=7.6Hz, 2H), 6.90 (d, J=8.6Hz, 2H), 6.67 (d, J=8.6Hz, 2H),
3.66(s,3H).13C NMR(100MHz,CDCl3)δ198.66,165.41,157.04,142.33,135.39,134.54,
134.29,131.41,129.27,128.87,128.76,127.98,122.26,113.95,55.27.HRMS(ESI)m/z[M+
H]+:Calcd for C21H18NO:316.1338.Found:316.1335.
The above is only presently preferred embodiments of the present invention, is not intended to limit the present invention in any form, any ripe
Professional and technical personnel is known, without departing from the scope of the present invention, according to the technical essence of the invention, to the above reality
Any simple modifications, equivalent substitutions and improvements etc. made by example are applied, it is fallen within the scope of protection of the technical scheme of the present invention
It is interior.
Claims (9)
1. a kind of method for being catalyzed benzalcohol derivatives amination, which is characterized in that by benzalcohol derivatives and amino benzenes compounds
Solvent and three pentafluorophenyl borane of catalyst is added in mixing, reacts 12-24 hours at 85 DEG C~120 DEG C and obtains benzylalcohol amination
Product.
2. the method according to claim 1, wherein the benzalcohol derivatives areWherein R1
Group is hydrogen atom, alkyl, aryl, ester group, halogen；R2 group is alkyl, aryl or cyano.
3. according to the method described in claim 2, it is characterized in that, the benzalcohol derivatives are benzhydrol and its similar
Object, benzyl carbinol and the like or benzaldehyde cyanohydrin.
4. method according to claim 1 or 2 or 3, which is characterized in that the amino benzenes compounds areR3 group
For methoxyl group, alkyl or aryl.
5. according to the method described in claim 4, it is characterized in that, the amino benzenes compounds are for P-nethoxyaniline or to first
Base aniline.
6. according to the method described in claim 5, it is characterized in that, mole of the benzalcohol derivatives and aromatic amine compounds
Than for 1:2.
7. according to the method described in claim 6, it is characterized in that, the additive amount molar percentage of the catalyst is 1%-
20%.
8. the method according to the description of claim 7 is characterized in that the molar ratio of the benzalcohol derivatives and catalyst is 1:
0.1。
9. according to the method described in claim 8, it is characterized in that, the solvent is nitromethane, toluene, 1,2- bis- chloroethene
Alkane, tetrahydrofuran or chloroform.
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| CN201810803944.0A CN109053460B (en) | 2018-07-20 | 2018-07-20 | Method for catalyzing amination of benzyl alcohol compound |
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| CN109053460B CN109053460B (en) | 2022-01-04 |
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| CN113735721A (en) * | 2021-10-09 | 2021-12-03 | 上海昕凯医药科技有限公司 | Method for synthesizing 3-ethylamino-4-methylphenol |
| CN115677568A (en) * | 2022-10-27 | 2023-02-03 | 南京晓庄学院 | One-step amination method of p-methylphenol |
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| CN109912579A (en) * | 2019-01-23 | 2019-06-21 | 华中科技大学 | A kind of preparation method of 2,2- disubstituted tetrahydrofuran derivatives |
| CN109912579B (en) * | 2019-01-23 | 2021-01-08 | 华中科技大学 | Preparation method of 2, 2-disubstituted tetrahydrofuran derivative |
| CN113735721A (en) * | 2021-10-09 | 2021-12-03 | 上海昕凯医药科技有限公司 | Method for synthesizing 3-ethylamino-4-methylphenol |
| CN113735721B (en) * | 2021-10-09 | 2023-09-29 | 上海昕凯医药科技有限公司 | Method for synthesizing 3-ethylamino-4-methylphenol |
| CN115677568A (en) * | 2022-10-27 | 2023-02-03 | 南京晓庄学院 | One-step amination method of p-methylphenol |
| CN115677568B (en) * | 2022-10-27 | 2024-04-19 | 南京晓庄学院 | One-step amination method of p-methylphenol |
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