CN107915670A - A kind of preparation method of 5 bromo indole - Google Patents
A kind of preparation method of 5 bromo indole Download PDFInfo
- Publication number
- CN107915670A CN107915670A CN201711068140.2A CN201711068140A CN107915670A CN 107915670 A CN107915670 A CN 107915670A CN 201711068140 A CN201711068140 A CN 201711068140A CN 107915670 A CN107915670 A CN 107915670A
- Authority
- CN
- China
- Prior art keywords
- indoles
- preparation
- bromo
- reaction
- catalyst
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention discloses a kind of preparation method of 5 bromo indole, comprise the following steps：2 sodium sulfonate, 1 acetylindole of preparation is dissolved in DMF; NBS (N bromosuccinimide) is added to be mixed; after reacting 2 3h at room temperature, it is 9 10 to add sodium hydroxide solution and adjust pH, is heated to 60 80 DEG C; after 8 12h of back flow reaction; pH is adjusted as neutrality, is evaporated under reduced pressure, filtering; solid matter is subjected to ethyl alcohol recrystallization, up to 5 bromo indole.The preparation method of the present invention is easy to operate, and reaction condition is gentle, environmentally protective, and accessory substance is less, and product purity is high, and product yield is higher.
Description
Technical field
The present invention relates to medicine intermediate field, more particularly to a kind of preparation method of 4- oxyindoles.
Background technology
Benzazole compounds are a kind of important branch in heterocyclic compound, it, with multiple biological activities, is nature
The middle most commonly used heterocyclic compound of distribution.Benzazole compounds are important Organic Chemicals and product, can be used as doctor
Medicine, pesticide, dyestuff, the intermediate of spices and other fine chemical products, have a wide range of applications in multiple fields.In medicine side
Face can synthesize antipyretic-antalgic agent, stimulant, depressor, vasodilator agent, antihistamine etc.；Also contain in many natural drugs
There is the dried venom of toads in indole structure, such as prepared Chinese traditional medicine liushen pill to contain 5-OHi derivative, contain indoles in a variety of alkaloids
Ring system structure；Common depressor reserpine is indole derivatives.In terms of pesticide, Benzazole compounds, which can be used as, efficiently plants
Thing growth regulator, fungicide etc., such as heteroauxin, indole -3-butyric acid be both important fabric regulator.In dye industry
In, the downstream product of indole derivatives can as the synthesis material of dyestuff, can produce azo dyes, phthalocyanine dye, sun from
Sub- dyestuff and indole methyl hydride dyestuff and a variety of new functionalized dyestuffs；Benzazole compounds are also used as photographic chemistry product, example
Such as synthesize photographic emulsion filter layer carbazole phthalein dyestuff.In terms of spices, indoles and 3- methyl indols are smelly with strong excrement
Taste but be the reconciliation for being usually used in artificial flower essential oil with the fragrance of a flower after diluting.
5- bromo indoles are a kind of important medicine intermediates, prevention and cure of cardiovascular disease, neurological disease, strengthen immunity with
And have in the medicine such as treatment tumour and be widely applied very much.The important source material of 5- bromo indoles or secondary colour aminated compounds, such as
Adjust circadian rhythm and the epiphysin of sleep.The production method of 5- bromo indoles is larger there are solvent-oil ratio at present, and cost is higher,
Conversion ratio it is relatively low and to environment it is unfriendly the problems such as.Therefore a kind of environmentally protective bromo indoles of 5- in high yield preparation side is researched and developed
Method, has higher practical value.
Chinese patent CN201410471023.0 provides a kind of green synthesis method of medicine intermediate 5- bromo indoles, bag
Include following steps：1. by indoles under the action of metallic catalyst, low-temp low-pressure liquid-phase hydrogenatin obtains indoline；2. indoline with
Acetylation reagent acts on, and generates N- acetylindole quinolines；3. N- acetylindoles quinoline generates N- acetyl by cleaning bromination reaction
Base -5--bromo indole quinolines；4. deacylation obtains 5--bromo indole quinolines to N- acetyl group -5--bromo indole quinolines in acid condition；5. 5- bromo indoles
Quinoline prepares crucial medicine intermediate 5- bromo indoles by oxidative dehydrogenation.Compared with prior art, which effectively controls 5- bromines Yin
Diindyl product bromo isomer, it is ensured that medical product security higher, reaction condition is gentle, and environmental pollution is small, and cost is low.
The content of the invention
The object of the present invention is to provide a kind of preparation method of 5- bromo indoles, the preparation method is easy to operate, reaction condition
Gently, environmentally protective, accessory substance is less, and product purity is high, and product yield is higher.
To achieve the above object, the present invention uses following technical scheme：
A kind of preparation method of 5- bromo indoles, comprises the following steps：
(1) by SO3It is passed through in ether, after mixing, adds catalyst, the ether that indoles is added dropwise under room temperature is molten
Liquid, is uniformly mixed, and after being added dropwise to complete after the reaction was continued 4-6h, adds sodium hydroxide solution thereto, stirring reaction 1-2h,
Generation precipitation, sediment is filtered, and is washed, and 2- sodium sulfonate indoles is made after dry；
(2) after the 2- sodium sulfonate indoles of preparation is mixed with acetic anhydride, under inert gas shielding, holding temperature is 50-
60 DEG C carry out reaction 4-5h, are cooled to room temperature, are filtered after the completion of reaction, washing, dry obtained 2- sodium sulfonate -1- acetyl group
Indoles；
(3) the 2- sodium sulfonate -1- acetylindoles of preparation are dissolved in DMF, add NBS (N-bromosuccinimide)
It is mixed, after reacting 2-3h at room temperature, it is 9-10 to add sodium hydroxide solution and adjust pH, is heated to 60-80 DEG C, reflux is anti-
After answering 8-12h, pH is adjusted as neutrality, is evaporated under reduced pressure, filtering, ethyl alcohol recrystallization is carried out by solid matter, up to the 5- bromines Yin
Diindyl.
Preferably, catalyst is ZrO in the step (1)2With diatomaceous mixture.
Preferably, catalyst is ZrO in the step (1)2It is 2 with diatomaceous mass ratio:3 mixture.
Preferably, the usage amount mass ratio of catalyst and indoles is 1 in the step (1)：1.
Preferably, indoles and SO in the step (1)3Usage amount molar ratio is 1:1.5-1.9.
Preferably, the mass concentration of sodium hydroxide solution is 30%-40% in the step (1).
Preferably, the usage amount molar ratio of 2- sodium sulfonates indoles and acetic anhydride is 1 in the step (2):15-20.
Preferably, the usage amount molar ratio of 2- sodium sulfonate -1- acetylindoles and NBS are 1 in the step (3):1.2-
1.8。
Preferably, the mass concentration of sodium hydroxide solution is 30-50% in the step (3).
The invention has the advantages that using SO3SO is formed with ether3- etherate, has higher stabilization
Property, carry out semi-annular jade pendant to indoles under catalyst using the complex, reaction is gentle, has higher selectivity, is conducive to
Suppress accessory substance, improve the purity of the 2- sodium sulfonate indoles of generation.Wherein catalyst uses ZrO2, should with diatomaceous mixture
Binary catalyst effectively raises the selectivity of semi-annular jade pendantization reaction, improves the yield of 2- sodium sulfonate indoles.Bromine is used as by the use of NBS
Agent carries out bromination reaction, and reaction process is more gentle, easily controllable, and reflection process is easy to operate, and accessory substance is less, and product is received
Rate is high.
Embodiment
In order to be better understood from the present invention, below by embodiment, the present invention is further described, and embodiment is served only for solving
The present invention is released, any restriction will not be formed to the present invention.
Embodiment 1
A kind of preparation method of 5- bromo indoles, comprises the following steps：
(1) by SO3It is passed through in ether, after mixing, adds catalyst, the ether that indoles is added dropwise under room temperature is molten
Liquid, is uniformly mixed, and after being added dropwise to complete after the reaction was continued 4h, adds sodium hydroxide solution, stirring reaction 1h, generation thereto
Precipitation, sediment is filtered, and is washed, and 2- sodium sulfonate indoles is made after dry；
(2) after the 2- sodium sulfonate indoles of preparation is mixed with acetic anhydride, under inert gas shielding, it is 50 DEG C to keep temperature
Reaction 4h is carried out, is cooled to room temperature, is filtered after the completion of reaction, is washed, dry obtained 2- sodium sulfonate -1- acetylindoles；
(3) the 2- sodium sulfonate -1- acetylindoles of preparation are dissolved in DMF, add NBS (N-bromosuccinimide)
It is mixed, after reacting 2h at room temperature, it is 9 to add sodium hydroxide solution and adjust pH, is heated to 60 DEG C, after back flow reaction 8h,
PH is adjusted as neutrality, is evaporated under reduced pressure, filtering, ethyl alcohol recrystallization is carried out by solid matter, up to the 5- bromo indoles.
Catalyst is ZrO in step (1)2It is 2 with diatomaceous mass ratio:3 mixture；The use of catalyst and indoles
It is 1 to measure mass ratio：1；Indoles and SO3Usage amount molar ratio is 1:1.5；The mass concentration of sodium hydroxide solution is 30%.
The usage amount molar ratio of 2- sodium sulfonates indoles and acetic anhydride is 1 in step (2):15.
The usage amount molar ratio of 2- sodium sulfonate -1- acetylindoles and NBS are 1 in step (3):1.2；Sodium hydroxide solution
Mass concentration be 30%.
The 5- bromo indoles yield of preparation is 93.5%, purity 99.5%.
Embodiment 2
A kind of preparation method of 5- bromo indoles, comprises the following steps：
(1) by SO3It is passed through in ether, after mixing, adds catalyst, the ether that indoles is added dropwise under room temperature is molten
Liquid, is uniformly mixed, and after being added dropwise to complete after the reaction was continued 6h, adds sodium hydroxide solution, stirring reaction 2h, generation thereto
Precipitation, sediment is filtered, and is washed, and 2- sodium sulfonate indoles is made after dry；
(2) after the 2- sodium sulfonate indoles of preparation is mixed with acetic anhydride, under inert gas shielding, it is 60 DEG C to keep temperature
Reaction 5h is carried out, is cooled to room temperature, is filtered after the completion of reaction, is washed, dry obtained 2- sodium sulfonate -1- acetylindoles；
(3) the 2- sodium sulfonate -1- acetylindoles of preparation are dissolved in DMF, add NBS (N-bromosuccinimide)
It is mixed, after reacting 3h at room temperature, it is 10 to add sodium hydroxide solution and adjust pH, is heated to 80 DEG C, back flow reaction 12h
Afterwards, pH is adjusted as neutrality, is evaporated under reduced pressure, and filtering, ethyl alcohol recrystallization is carried out by solid matter, up to the 5- bromo indoles.
Catalyst is ZrO in step (1)2It is 2 with diatomaceous mass ratio:3 mixture；The use of catalyst and indoles
It is 1 to measure mass ratio：1；Indoles and SO3Usage amount molar ratio is 1:1.9；The mass concentration of sodium hydroxide solution is 40%.
The usage amount molar ratio of 2- sodium sulfonates indoles and acetic anhydride is 1 in step (2):20.
The usage amount molar ratio of 2- sodium sulfonate -1- acetylindoles and NBS are 1 in step (3):1.8；Sodium hydroxide solution
Mass concentration be 50%.
The 5- bromo indoles yield of preparation is 94.1%, purity 99.5%.
Embodiment 3
A kind of preparation method of 5- bromo indoles, comprises the following steps：
(1) by SO3It is passed through in ether, after mixing, adds catalyst, the ether that indoles is added dropwise under room temperature is molten
Liquid, is uniformly mixed, and after being added dropwise to complete after the reaction was continued 4h, adds sodium hydroxide solution, stirring reaction 2h, generation thereto
Precipitation, sediment is filtered, and is washed, and 2- sodium sulfonate indoles is made after dry；
(2) after the 2- sodium sulfonate indoles of preparation is mixed with acetic anhydride, under inert gas shielding, it is 50 DEG C to keep temperature
Reaction 5h is carried out, is cooled to room temperature, is filtered after the completion of reaction, is washed, dry obtained 2- sodium sulfonate -1- acetylindoles；
(3) the 2- sodium sulfonate -1- acetylindoles of preparation are dissolved in DMF, add NBS (N-bromosuccinimide)
It is mixed, after reacting 2h at room temperature, it is 10 to add sodium hydroxide solution and adjust pH, is heated to 60-80 DEG C, back flow reaction 8h
Afterwards, pH is adjusted as neutrality, is evaporated under reduced pressure, and filtering, ethyl alcohol recrystallization is carried out by solid matter, up to the 5- bromo indoles.
Catalyst is ZrO in step (1)2It is 2 with diatomaceous mass ratio:3 mixture；The use of catalyst and indoles
It is 1 to measure mass ratio：1；Indoles and SO3Usage amount molar ratio is 1:1.9；The mass concentration of sodium hydroxide solution is 30%.
The usage amount molar ratio of 2- sodium sulfonates indoles and acetic anhydride is 1 in step (2):20.
The usage amount molar ratio of 2- sodium sulfonate -1- acetylindoles and NBS are 1 in step (3):1.2；Sodium hydroxide solution
Mass concentration be 50%.
The 5- bromo indoles yield of preparation is 95.2%, purity 99.5%
Embodiment 4
A kind of preparation method of 5- bromo indoles, comprises the following steps：
(1) by SO3It is passed through in ether, after mixing, adds catalyst, the ether that indoles is added dropwise under room temperature is molten
Liquid, is uniformly mixed, and after being added dropwise to complete after the reaction was continued 6h, adds sodium hydroxide solution, stirring reaction 1h, generation thereto
Precipitation, sediment is filtered, and is washed, and 2- sodium sulfonate indoles is made after dry；
(2) after the 2- sodium sulfonate indoles of preparation is mixed with acetic anhydride, under inert gas shielding, it is 60 DEG C to keep temperature
Reaction 4h is carried out, is cooled to room temperature, is filtered after the completion of reaction, is washed, dry obtained 2- sodium sulfonate -1- acetylindoles；
(3) the 2- sodium sulfonate -1- acetylindoles of preparation are dissolved in DMF, add NBS (N-bromosuccinimide)
It is mixed, after reacting 3h at room temperature, it is 9 to add sodium hydroxide solution and adjust pH, is heated to 80 DEG C, after back flow reaction 8h,
PH is adjusted as neutrality, is evaporated under reduced pressure, filtering, ethyl alcohol recrystallization is carried out by solid matter, up to the 5- bromo indoles.
Catalyst is ZrO in step (1)2It is 2 with diatomaceous mass ratio:3 mixture；The use of catalyst and indoles
It is 1 to measure mass ratio：1；Indoles and SO3Usage amount molar ratio is 1:1.5；The mass concentration of sodium hydroxide solution is 40%.
The usage amount molar ratio of 2- sodium sulfonates indoles and acetic anhydride is 1 in step (2):15.
The usage amount molar ratio of 2- sodium sulfonate -1- acetylindoles and NBS are 1 in step (3)：1.8；Sodium hydroxide solution
Mass concentration be 30%.
The 5- bromo indoles yield of preparation is 94.9%, purity 99.5%.
Embodiment 5
A kind of preparation method of 5- bromo indoles, comprises the following steps：
(1) by SO3It is passed through in ether, after mixing, adds catalyst, the ether that indoles is added dropwise under room temperature is molten
Liquid, is uniformly mixed, and after being added dropwise to complete after the reaction was continued 5h, adds sodium hydroxide solution, stirring reaction 2h, generation thereto
Precipitation, sediment is filtered, and is washed, and 2- sodium sulfonate indoles is made after dry；
(2) after the 2- sodium sulfonate indoles of preparation is mixed with acetic anhydride, under inert gas shielding, it is 50 DEG C to keep temperature
Reaction 5h is carried out, is cooled to room temperature, is filtered after the completion of reaction, is washed, dry obtained 2- sodium sulfonate -1- acetylindoles；
(3) the 2- sodium sulfonate -1- acetylindoles of preparation are dissolved in DMF, add NBS (N-bromosuccinimide)
It is mixed, after reacting 3h at room temperature, it is 9 to add sodium hydroxide solution and adjust pH, is heated to 70 DEG C, after back flow reaction 10h,
PH is adjusted as neutrality, is evaporated under reduced pressure, filtering, ethyl alcohol recrystallization is carried out by solid matter, up to the 5- bromo indoles.
Catalyst is ZrO in step (1)2It is 2 with diatomaceous mass ratio:3 mixture；The use of catalyst and indoles
It is 1 to measure mass ratio：1；Indoles and SO3Usage amount molar ratio is 1:1.7；The mass concentration of sodium hydroxide solution is 35%.
The usage amount molar ratio of 2- sodium sulfonates indoles and acetic anhydride is 1 in step (2):17.
The usage amount molar ratio of 2- sodium sulfonate -1- acetylindoles and NBS are 1 in step (3):1.5；Sodium hydroxide solution
Mass concentration be 40%.
The 5- bromo indoles yield of preparation is 94.5%, purity 99.5%.
Claims (9)
1. a kind of preparation method of 5- bromo indoles, it is characterised in that comprise the following steps：
(1) by SO3It is passed through in ether, after mixing, adds catalyst, the diethyl ether solution of indoles, stirring is added dropwise under room temperature
It is uniformly mixed, after being added dropwise to complete after the reaction was continued 4-6h, adds sodium hydroxide solution thereto, stirring reaction 1-2h, generation is heavy
Form sediment, sediment is filtered, wash, 2- sodium sulfonate indoles is made after dry；
(2) after the 2- sodium sulfonate indoles of preparation is mixed with acetic anhydride, under inert gas shielding, it is 50-60 DEG C to keep temperature
Reaction 4-5h is carried out, is cooled to room temperature, is filtered after the completion of reaction, is washed, dry obtained 2- sodium sulfonate -1- acetyl group Yin
Diindyl；
(3) the 2- sodium sulfonate -1- acetylindoles of preparation are dissolved in DMF, add NBS (N-bromosuccinimide) mixing
Stirring, after reacting 2-3h at room temperature, it is 9-10 to add sodium hydroxide solution and adjust pH, is heated to 60-80 DEG C, back flow reaction 8-
After 12h, pH is adjusted as neutrality, is evaporated under reduced pressure, filtering, ethyl alcohol recrystallization is carried out by solid matter, up to the 5- bromo indoles.
2. the preparation method of 5- bromo indoles according to claim 1, it is characterised in that：Catalyst is in the step (1)
ZrO2With diatomaceous mixture.
3. the preparation method of 5- bromo indoles according to claim 1, it is characterised in that：Catalyst is in the step (1)
ZrO2It is 2 with diatomaceous mass ratio:3 mixture.
4. the preparation method of 5- bromo indoles according to claim 1, it is characterised in that：In the step (1) catalyst with
The usage amount mass ratio of indoles is 1：1.
5. the preparation method of 5- bromo indoles according to claim 1, it is characterised in that：Indoles and SO in the step (1)3
Usage amount molar ratio is 1:1.5-1.9.
6. the preparation method of 5- bromo indoles according to claim 1, it is characterised in that：Sodium hydroxide in the step (1)
The mass concentration of solution is 30%-40%.
7. the preparation method of 5- bromo indoles according to claim 1, it is characterised in that：2- sodium sulfonates in the step (2)
The usage amount molar ratio of indoles and acetic anhydride is 1:15-20.
8. the preparation method of 5- bromo indoles according to claim 1, it is characterised in that：2- sodium sulfonates in the step (3)-
The usage amount molar ratio of 1- acetylindoles and NBS are 1:1.2-1.8.
9. the preparation method of 5- bromo indoles according to claim 1, it is characterised in that：Sodium hydroxide in the step (3)
The mass concentration of solution is 30-50%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711068140.2A CN107915670A (en) | 2017-11-03 | 2017-11-03 | A kind of preparation method of 5 bromo indole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711068140.2A CN107915670A (en) | 2017-11-03 | 2017-11-03 | A kind of preparation method of 5 bromo indole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107915670A true CN107915670A (en) | 2018-04-17 |
Family
ID=61895226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711068140.2A Withdrawn CN107915670A (en) | 2017-11-03 | 2017-11-03 | A kind of preparation method of 5 bromo indole |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107915670A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102558017A (en) * | 2011-12-27 | 2012-07-11 | 郑州凯美克化学有限公司 | Method for preparing 5-bromoindole |
| CN103183629A (en) * | 2013-03-15 | 2013-07-03 | 张家港威胜生物医药有限公司 | Process of effectively synthesizing important pharmaceutical and chemical intermediate 5-bromoindole |
| CN105622481A (en) * | 2014-10-28 | 2016-06-01 | 赵建英 | Process for efficient synthesis of 5-bromoindole |
-
2017
- 2017-11-03 CN CN201711068140.2A patent/CN107915670A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102558017A (en) * | 2011-12-27 | 2012-07-11 | 郑州凯美克化学有限公司 | Method for preparing 5-bromoindole |
| CN103183629A (en) * | 2013-03-15 | 2013-07-03 | 张家港威胜生物医药有限公司 | Process of effectively synthesizing important pharmaceutical and chemical intermediate 5-bromoindole |
| CN105622481A (en) * | 2014-10-28 | 2016-06-01 | 赵建英 | Process for efficient synthesis of 5-bromoindole |
Non-Patent Citations (2)
| Title |
|---|
| 刘平等: "一种5-羟基吲哚制备新工艺", 《广东化工》 * |
| 姬明理等: "5-甲氧基吲哚的合成", 《精细化工中间体》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105669529B (en) | A kind of fulleropyrrolidine derivative and preparation method thereof | |
| CN104610071B (en) | A kind of chlorine direct chlorination and hydrogen peroxide oxidation chlorination are prepared the method for 2,6-Dichloro-4-nitroaniline simultaneously | |
| CN104529896B (en) | Synthetic method of diaryl substituted isoquinoline compound | |
| CN109232411B (en) | Method for preparing boscalid | |
| CN107382864A (en) | A kind of licochalcone A pyrazoline Carbox amide and its synthetic method for having antitumor activity | |
| CN107522584B (en) | Alpha-trifluoromethyl ketone compound and preparation method thereof | |
| CN106242990A (en) | A kind of preparation method of 2 amino 4 acetyl-anisidines | |
| CN107915670A (en) | A kind of preparation method of 5 bromo indole | |
| CN106366036A (en) | 6, 9-bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5, 10-dione dimaleate and synthesis technology thereof | |
| CN108440375A (en) | Using disulfide as the catalysis oxidation synthetic method of the 3- sulfydryl indole class compounds of sulphur source | |
| CN110885570B (en) | Preparation method of near-infrared dye | |
| CN108047138A (en) | Preparation method without hydrazine N-BETA-Alanyl-L-histidine | |
| CN108101800A (en) | A kind of synthetic method of ortho-aminobenzoic acid | |
| CN101239983A (en) | Chiral synthesis method for (-)-galantamin hydrobromide | |
| CN105693778B (en) | The method of N- methoxymethylamide guiding synthesis ferrocene and Pyridione derivatives | |
| CN111233045B (en) | Method for preparing iron oxide red pigment and synchronously producing aromatic amine | |
| CN110590652B (en) | Synthesis method of 2-amino-5-iodopyridine | |
| CN107383418A (en) | A kind of unioresistant plastic additive and preparation method thereof | |
| CN106748816A (en) | A kind of synthetic method of the amino butanol of Du Lutewei key intermediates (R) 3 | |
| CN102424658B (en) | Synthetic method of benzene dinitrile or substituted benzene dinitrile | |
| CN106749007B (en) | A method of preparing 7- hydroxyl -2- quinolone | |
| CN107954917A (en) | A kind of preparation method of 4- oxyindoles | |
| CN105541590B (en) | A kind of synthetic method for being fluorinated compound of fluorene class | |
| CN110343053A (en) | A kind of preparation method of ultraviolet absorbing agent | |
| CN107915652A (en) | A kind of preparation method of 8 acetylamino, 2 naphthols |
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 | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20180417 |