CN106946920A - A kind of preparation method of 4 amino phenyl boronic acid derivative - Google Patents
A kind of preparation method of 4 amino phenyl boronic acid derivative Download PDFInfo
- Publication number
- CN106946920A CN106946920A CN201710218099.6A CN201710218099A CN106946920A CN 106946920 A CN106946920 A CN 106946920A CN 201710218099 A CN201710218099 A CN 201710218099A CN 106946920 A CN106946920 A CN 106946920A
- Authority
- CN
- China
- Prior art keywords
- amino phenyl
- boronic acid
- preparation
- acid derivative
- phenyl boronic
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- ZSKXYSCQDWAUCM-UHFFFAOYSA-N 1-(chloromethyl)-2-dodecylbenzene Chemical class CCCCCCCCCCCCC1=CC=CC=C1CCl ZSKXYSCQDWAUCM-UHFFFAOYSA-N 0.000 title abstract 3
- 230000009467 reduction Effects 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 5
- 238000005917 acylation reaction Methods 0.000 claims abstract description 5
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 3
- MKPDAJWEBQRQCO-UHFFFAOYSA-N (4-aminophenyl)boronic acid Chemical class NC1=CC=C(B(O)O)C=C1 MKPDAJWEBQRQCO-UHFFFAOYSA-N 0.000 claims description 19
- 238000005984 hydrogenation reaction Methods 0.000 claims description 13
- ZPKSAIWDCQVXSQ-UHFFFAOYSA-N (4-aminophenoxy)boronic acid Chemical class NC1=CC=C(OB(O)O)C=C1 ZPKSAIWDCQVXSQ-UHFFFAOYSA-N 0.000 claims description 10
- LBAHHHQOJMMVQK-UHFFFAOYSA-N OBO.[O-][N+](=O)C1=CC=CC=C1 Chemical class OBO.[O-][N+](=O)C1=CC=CC=C1 LBAHHHQOJMMVQK-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- VYEWTHXZHHATTA-UHFFFAOYSA-N (4-acetamidophenyl)boronic acid Chemical group CC(=O)NC1=CC=C(B(O)O)C=C1 VYEWTHXZHHATTA-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical group ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical group CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004040 pyrrolidinones Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- YWTZZWYYDUCDLZ-UHFFFAOYSA-N boric acid;nitrobenzene Chemical compound OB(O)O.[O-][N+](=O)C1=CC=CC=C1 YWTZZWYYDUCDLZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 claims 1
- -1 methyl benzoyl amino Chemical group 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 238000002474 experimental method Methods 0.000 abstract description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000012827 research and development Methods 0.000 abstract description 2
- UMOPBIVXPOETPG-UHFFFAOYSA-N (2-acetamidophenyl)boronic acid Chemical class CC(=O)NC1=CC=CC=C1B(O)O UMOPBIVXPOETPG-UHFFFAOYSA-N 0.000 abstract 1
- DIRRKLFMHQUJCM-UHFFFAOYSA-N (2-aminophenyl)boronic acid Chemical class NC1=CC=CC=C1B(O)O DIRRKLFMHQUJCM-UHFFFAOYSA-N 0.000 abstract 1
- 235000010338 boric acid Nutrition 0.000 abstract 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 abstract 1
- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical class OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000005909 ethyl alcohol group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NSFJAFZHYOAMHL-UHFFFAOYSA-N (4-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=C([N+]([O-])=O)C=C1 NSFJAFZHYOAMHL-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- XNNKQIPMIAMBJO-UHFFFAOYSA-N aniline;boron Chemical compound [B].NC1=CC=CC=C1 XNNKQIPMIAMBJO-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to pharmaceutical intermediate preparing technical field, and in particular to a kind of preparation method of 4 amino phenyl boronic acid derivative.Preparation method preparation method first is using 4 nitrobenzene boronic acids as raw material first; 4 amino phenyl boric acids are obtained by hydrogenating reduction; then acylation reaction; the 4 amino phenyl boronic acid derivatives such as 4 acetamidobenzeneboronic acids, 4 (N is to methyl benzoyl amino) phenyl boric acids are obtained, and product is analyzed and characterized.Advantage of the invention is that：The yield of 4 prepared amino phenyl boronic acid derivatives is high, and preparation technology is simple, and mild condition, energy consumption is low, low cost, is adapted to produce in enormous quantities, reliable experiment basis are provided for the research and development of downstream product.
Description
Technical field
The invention belongs to pharmaceutical intermediate preparing technical field, and in particular to a kind of preparation of 4- amino phenyl boronic acid derivative
Method.
Background technology
4- amino phenyl boronic acid derivative is played very as a kind of active intermediate in organic synthesis and field of medicaments
Important effect, this be mainly based upon its good stability, it is cheap, with electrophilic group and environmentally friendly etc. many excellent
Point, while it can be used for preparing the fluorescence chromophore molecule for possessing and adapting to physiological environment, the benzene such as anthracene class, naphthalenes, heterocyclic
Boronic acid compounds, and its chromatography, mould detection and new PH sensors in be also widely used.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of preparation method of 4- amino phenyl boronic acid derivative.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：A kind of preparation side of 4- amino phenyl boronic acid derivative
Method, it comprises the following steps：4- nitrobenzene boronic acids generation hydrogenating reduction under atmosphere of hydrogen and palladium-carbon catalyst effect first is anti-
4- amino phenyl boric acids should be obtained, then 4- amino phenyl boric acid gives birth to acylation reaction with acylting agent hybrid concurrency in a solvent,
Produce the 4- amino phenyl boronic acid derivative.
On the basis of above-mentioned technical proposal, the present invention can also do specifically chosen or optimum choice further below.
Specifically, 4- nitrobenzene boronic acid hydrogenation reductions are carried out in hydrogenation reaction kettle, by 4- nitrobenzene boronic acids and nothing
Water-ethanol is according to 1mol:10-30mL amount ratio mixing, then adds the palladium of the 0.02-0.1 times of 4- nitrobenzene boronic acids weight
Hydrogen Vapor Pressure is 0.2-1atm (1atm in C catalyst (effective ingredient metal palladium content is 0.5wt%), the hydrogenation reaction kettle
Represent a standard atmospheric pressure), the reaction time of hydrogenation reduction is 1-6h.
Specifically, when the acylting agent is chloroacetic chloride, acetic anhydride or acetic acid, obtained 4- amino phenyl boronic acid derivatives
For 4- acetamidobenzeneboronic acids, when the acylting agent is 4- methyl benzoyl chlorides, obtained 4- amino phenyl boronic acid derivatives
For 4- (N- is to methyl benzoyl amino) phenyl boric acid..
Specifically, described solvent is tetrahydrofuran, chloroform, dichloroethanes, dichloromethane or the pyrroles of N- methyl -2
Alkanone.
It is preferred that, the mol ratio of 4- amino phenyl boric acid and acylting agent is 1：1-3, the reaction temperature of acylation reaction is
20-40 DEG C, the reaction time is 3-8h.
Compared with prior art, the beneficial effects of the invention are as follows：The method provided by the present invention prepares 4- aminobenzene boron
The yield of acid derivative is high, cheap and easy to get using 4- nitrobenzene boronic acids as raw material, whole preparation process relatively simple and mild condition,
Energy consumption is low, low cost, is adapted to produce in enormous quantities, reliable experiment basis are provided for the research and development of downstream product.
Embodiment
The present invention is described in further detail below in conjunction with specific embodiment, example is served only for explaining this hair
It is bright, it is not intended to limit the scope of the present invention.
Medicine used is commercially available prod unless otherwise noted in following examples, and method therefor is unless otherwise noted
Conventional method.
Embodiment 1
A kind of preparation method of 4- amino phenyl boronic acid derivative (4- acetamidobenzeneboronic acids), it comprises the following steps:
16.7g (0.1mol) 4- nitrobenzene boronic acids and 200mL absolute ethyl alcohols are added in hydrogenation reaction kettle, then added
1.67g palladium carbons (0.5%), with nitrogen displacement 5 times, are then heated to reflux, Hydrogen Vapor Pressure is 0.5atm, after reaction 3h, cooling, mistake
Recycling design after filter, produces 135g white solid powder 4- amino phenyl boric acids, yield 98.7%, and fusing point is：62-66℃；1H-
NMR (400MHz, CD3OD)δ(ppm)：7.76-7.73 (m, 2H), 7.68-7.63 (m, 2H), 4.76 (br s, 2H), 1.33-
1.38(s,2H)；FAB-MS(m/z)：138[M+H]+。
13.7g (0.1mol) 4- amino phenyl boric acid and 50mL tetrahydrofurans are added in there-necked flask, is sufficiently stirred for rear cold
But to 10 DEG C, 11.7g (0.15mol) chloroacetic chloride is then added dropwise, drop finishes, the stirring reaction 5h at 25 DEG C adds 150mL water, stirred
Mixing i.e. has solid wash-off, filtration drying, obtain 13g white or white solid powder 4- acetamidobenzeneboronic acids, yield 72.6%,
Fusing point is：216-220℃；FT-IR (KBr compressing tablets, σ cm-1)：3311,3048,1674,1610,1588；1H-NMR (400MHz,
CD3OD)δ(ppm)：7.77-7.74 (m, 2H), 7.65-7.67 (m, 2H), 4.77 (br s, 2H), 4.21-4.26 (s, 3H),
1.35-1.38(s,1H)；FAB-MS(m/z)：180[M+H]+。
Embodiment 2
A kind of preparation method of 4- amino phenyl boronic acid derivative (4- acetamidobenzeneboronic acids), it comprises the following steps:
16.7g (0.1mol) 4- nitrobenzene boronic acids and 100mL absolute ethyl alcohols are added in hydrogenation reaction kettle, then added
0.334g palladium carbons (palladium content 0.5wt%), with nitrogen displacement 5 times, are then heated to reflux, Hydrogen Vapor Pressure is 0.2atm, react 6h
Afterwards, cool down, recycling design after filtering produces 132g white solid powder 4- amino phenyl boric acids, yield 96.5%, and fusing point is：62-
66℃；1H-NMR (400MHz, CD3OD)δ(ppm)：7.76-7.73 (m, 2H), 7.68-7.63 (m, 2H), 4.76 (br s, 2H),
1.33-1.38(s,2H)；FAB-MS(m/z)：138[M+H]+。
13.7g (0.1mol) 4- amino phenyl boric acid and 100mL chloroforms are added in there-necked flask, is sufficiently stirred for rear cold
But to 5 DEG C, 23.4g (0.3mol) chloroacetic chloride is then added dropwise, drop finishes, the stirring reaction 3h at 40 DEG C, adds 150mL water, stirring
There is solid wash-off, filtration drying obtains 14g whites or white solid powder 4- acetamidobenzeneboronic acids, and yield 78.2% melts
Put and be：216-220℃；FT-IR (KBr compressing tablets, σ cm-1)：3311,3048,1674,1610,1588；1H-NMR (400MHz,
CD3OD)δ(ppm)：7.77-7.74 (m, 2H), 7.65-7.67 (m, 2H), 4.77 (br s, 2H), 4.21-4.26 (s, 3H),
1.35-1.38(s,1H)；FAB-MS(m/z)：180[M+H]+。
Embodiment 3
A kind of preparation method of 4- amino phenyl boronic acid derivative [4- (N- is to methyl benzoyl amino) phenyl boric acid], it is wrapped
Include following steps:
16.7g (0.1mol) 4- nitrobenzene boronic acids and 300mL absolute ethyl alcohols are added in hydrogenation reaction kettle, then added
0.835g palladium carbons (palladium content 0.5wt%), with nitrogen displacement 5 times, are then heated to reflux, Hydrogen Vapor Pressure is 1atm, after reaction 4h,
Cooling, recycling design after filtering produces 129.7g white solid powder 4- amino phenyl boric acids, yield 94.8%, and fusing point is：62-
66℃；1H-NMR (400MHz, CD3OD)δ(ppm)：7.76-7.73 (m, 2H), 7.68-7.63 (m, 2H), 4.76 (br s, 2H),
1.33-1.38(s,2H)；FAB-MS(m/z)：138[M+H]+。
13.7g (0.1mol) 4- amino phenyl boric acid and the pyrrolidones of 80mL N- methyl -2 are added in there-necked flask
(NMP) 10 DEG C are cooled to after, being sufficiently stirred for, 23.3g (0.15mol) 4- methyl benzoyl chlorides are then added dropwise, drop finishes, at 30 DEG C
Stirring reaction 4h, adds 150mL water, and stirring has solid wash-off, and filtration drying obtains 193g whites or white solid powder 4-
(N- is to methyl benzoyl amino) phenyl boric acid, yield 75.8%, FT-IR (KBr compressing tablets, σ cm-1)：3310,3045,1659,
1605,1590；1H-NMR (400MHz, CD3OD)δ(ppm)：7.92-7.85(m,2H),7.76-7.74(m,2H),7.68-7.61
(m, 2H), 7.61-7.46 (m, 2H), 4.74 (br s, 2H), 4.22-4.25 (s, 3H), 1.35-1.36 (s, 1H)；；FAB-MS
(m/z)：278[M+Na]+。
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and
Within principle, any modifications, equivalent substitutions and improvements made etc. should be included within the scope of the present invention.
Claims (5)
1. a kind of preparation method of 4- amino phenyl boronic acid derivative, it is characterised in that comprise the following steps：4- nitrobenzene boron first
Acid occurs hydrogenation reduction under atmosphere of hydrogen and palladium-carbon catalyst effect and obtains 4- amino phenyl boric acids, then 4- aminobenzenes boron
Acid gives birth to acylation reaction with acylting agent hybrid concurrency in a solvent, produces the 4- amino phenyl boronic acid derivative.
2. a kind of preparation method of 4- amino phenyl boronic acid derivative according to claim 1, it is characterised in that 4- nitrobenzene
Boric acid hydrogenation reduction is carried out in hydrogenation reaction kettle, by 4- nitrobenzene boronic acids and absolute ethyl alcohol according to 0.1mol:100-
300mL amount ratio is added in the hydrogenation reaction kettle and mixed, and then adds the 0.02-0.1 times of 4- nitrobenzene boronic acids weight
Hydrogen Vapor Pressure is 0.2-1atm in the palladium-carbon catalyst of amount, the hydrogenation reaction kettle, and the reaction time of hydrogenation reduction is 1-
6h。
3. a kind of preparation method of 4- amino phenyl boronic acid derivative according to claim 1, it is characterised in that the acyl group
When change reagent is chloroacetic chloride, acetic anhydride or acetic acid, obtained 4- amino phenyl boronic acid derivative is 4- acetamidobenzeneboronic acids, described
When acylting agent is 4- methyl benzoyl chlorides, obtained 4- amino phenyl boronic acid derivative is that (N- is to methyl benzoyl ammonia by 4-
Base) phenyl boric acid.
4. a kind of preparation method for the 4- amino phenyl boronic acid derivative stated according to claim 1, it is characterised in that described solvent
For tetrahydrofuran, chloroform, dichloroethanes, dichloromethane or the pyrrolidones of N- methyl -2.
5. a kind of preparation method of 4- amino phenyl boronic acid derivative according to any one of Claims 1-4, its feature exists
In the mol ratio of 4- amino phenyl boric acid and acylting agent is 1：1-3, the reaction temperature of acylation reaction is 20-40 DEG C, reaction
Time is 3-8h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710218099.6A CN106946920A (en) | 2017-04-05 | 2017-04-05 | A kind of preparation method of 4 amino phenyl boronic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710218099.6A CN106946920A (en) | 2017-04-05 | 2017-04-05 | A kind of preparation method of 4 amino phenyl boronic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106946920A true CN106946920A (en) | 2017-07-14 |
Family
ID=59474360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710218099.6A Pending CN106946920A (en) | 2017-04-05 | 2017-04-05 | A kind of preparation method of 4 amino phenyl boronic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106946920A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110330691A (en) * | 2019-07-23 | 2019-10-15 | 华侨大学 | A kind of alkyl system dynamic crosslinking agent and its application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1293665A (en) * | 1998-02-18 | 2001-05-02 | 神经研究公司 | New compounds and their use as positive AMPA receptor modulators |
| CN103965170A (en) * | 2013-01-24 | 2014-08-06 | 通化济达医药有限公司 | Benzene sulfonamide pyrazole kinase inhibitor |
-
2017
- 2017-04-05 CN CN201710218099.6A patent/CN106946920A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1293665A (en) * | 1998-02-18 | 2001-05-02 | 神经研究公司 | New compounds and their use as positive AMPA receptor modulators |
| CN103965170A (en) * | 2013-01-24 | 2014-08-06 | 通化济达医药有限公司 | Benzene sulfonamide pyrazole kinase inhibitor |
Non-Patent Citations (1)
| Title |
|---|
| WILLIAM ERB,ET AL.: ""Sequential One-Pot Access to Molecular Diversity through Aniline Aqueous Borylation"", 《J. ORG. CHEM.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110330691A (en) * | 2019-07-23 | 2019-10-15 | 华侨大学 | A kind of alkyl system dynamic crosslinking agent and its application |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Samzadeh-Kermani | Ethynylation of isoquinoline and quinoline derivatives with calcium carbide | |
| Xiao et al. | MOF-5 as a highly efficient and recyclable catalyst for one pot synthesis of 2, 4-disubstituted quinoline derivatives | |
| CN102863361B (en) | Chiral catalytic synthesis method of thiamphenicol | |
| CN106946920A (en) | A kind of preparation method of 4 amino phenyl boronic acid derivative | |
| CN102285909B (en) | Preparation method of benzpyrole-2-ketone compound | |
| CN112552224A (en) | Synthesis method of 4-hydroxyindole | |
| CN107353245A (en) | A kind of synthetic method of quinolines | |
| CN108147946A (en) | A kind of method for preparing 4- phenylphenols | |
| CN112209935B (en) | Preparation method of pyrazino-fused quinazolinone substance | |
| CN110818709B (en) | CO (carbon monoxide) 2 Method for synthesizing pyrimidinone compounds | |
| CN108440391B (en) | A kind of preparation method of 2,4,6- triaryl substituted pyridine derivative | |
| CN107382640B (en) | β -aryl phenylpropanone compound synthesis method | |
| CN113548965A (en) | Preparation method of 1, 4-eneyne compound | |
| CN105949079A (en) | Method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis | |
| CN106749235A (en) | The preparation method of poly-substituted quinoline and azole derivatives | |
| CN110229096B (en) | Preparation method of 2, 6-pyridinedicarboxylic acid | |
| CN100415707C (en) | Method for preparing anchoic acid by microwave reaction | |
| CN104788324A (en) | Synthetic method of aminofluorene compounds | |
| CN110041374A (en) | A kind of preparation method of palladium complex | |
| CN107759499B (en) | The method for synthesizing alpha, beta-unsaturated ketone compound is modified by acetophenone derivs α-H is Bifunctionalized | |
| CN103804350B (en) | A kind of preparation method of high purity pool horse degree amine | |
| CN105418393B (en) | Two step one-pot synthesis methods of meta position substituted benzophenone class compound | |
| CN109265403A (en) | A kind of synthetic method of benzimidazole and its derivative | |
| CN108863900A (en) | A kind of preparation method of 5- fluoro indole -2- ketone | |
| CN1311185A (en) | Method for preparing 4-amino pyridine and its derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170714 |
|
| RJ01 | Rejection of invention patent application after publication |