CN117069654A - Method for synthesizing 2-methylquinoline by taking paraldehyde as raw material - Google Patents
Method for synthesizing 2-methylquinoline by taking paraldehyde as raw material Download PDFInfo
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- CN117069654A CN117069654A CN202311313247.4A CN202311313247A CN117069654A CN 117069654 A CN117069654 A CN 117069654A CN 202311313247 A CN202311313247 A CN 202311313247A CN 117069654 A CN117069654 A CN 117069654A
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- Prior art keywords
- paraldehyde
- iodine
- methylquinoline
- synthesizing
- containing compound
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Links
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 30
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 229960003868 paraldehyde Drugs 0.000 title claims abstract description 23
- 239000002994 raw material Substances 0.000 title claims abstract description 11
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 15
- 239000011630 iodine Substances 0.000 claims abstract description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007800 oxidant agent Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 230000001590 oxidative effect Effects 0.000 claims abstract description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 claims description 2
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 2
- 229940107816 ammonium iodide Drugs 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 claims description 2
- 229940078552 o-xylene Drugs 0.000 claims description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 2
- 235000009518 sodium iodide Nutrition 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 229960002317 succinimide Drugs 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 229910052723 transition metal Inorganic materials 0.000 abstract description 5
- 150000003624 transition metals Chemical class 0.000 abstract description 5
- 230000007547 defect Effects 0.000 abstract description 4
- 238000001308 synthesis method Methods 0.000 abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 abstract description 3
- -1 2-methylquinoline compound Chemical class 0.000 abstract description 2
- 238000006555 catalytic reaction Methods 0.000 abstract description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000007797 corrosion Effects 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005648 named reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006273 synthetic pesticide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Abstract
The invention provides a method for synthesizing 2-methylquinoline by taking paraldehyde as a raw material, which belongs to the field of chemical synthesis, uses an iodine-containing compound as a catalyst, uses a green oxidant as an oxidant, and uses aniline, the iodine-containing compound or elemental iodine, wherein the molar ratio of the paraldehyde is 1:0.05-0.5:7-56; the volume ratio of the paraldehyde to the solvent is 1:0-0.5. The method overcomes the defects of inorganic acid which needs a large amount of corrosion equipment, or transition metal catalysis and the like in the existing method for synthesizing the 2-methylquinoline compound, greatly improves the greenness of the synthesis method, and has the advantages of simple reaction system, mild condition, wide raw material source, low price, high yield, easy expansion of application and the like.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a method for synthesizing 2-methylquinoline by taking paraldehyde as a raw material.
Background
The 2-methylquinoline is an important chemical intermediate, can be complexed with metal ions, is used for measuring metal bismuth, can be used for synthesizing quinoline dye such as quinoline red and the like, can be also used for a vulcanization accelerator of rubber, and has wide application in the fields of pesticides such as synthetic pesticides, bactericides and the like, and has wide development prospect.
The currently reported synthetic methods of 2-methylquinoline mainly comprise the following steps: the method comprises the steps of firstly, a coal tar extraction method, namely, obtaining 2-methylquinoline by taking coal tar or isoquinoline kettle residues as raw materials through multi-step treatment, wherein the method has the defects of generating a large amount of wastewater and having low product yield; the second method mainly comprises Skraup method, dback-von Miller method, combes method, friedl ä nd method, pfitzinger method and the like by traditional name reaction synthesis methods, wherein the main defects of the methods are that a large amount of inorganic acid and alkali are used, a large amount of waste is generated, and the yield is not high; the method III uses transition metal to catalyze and synthesize 2-methylquinoline, and the method has the defects that the transition metal catalyst is relatively expensive and the environment is easy to pollute; there are also methods for synthesizing 2-methylquinoline using a solid acid catalyst or the like, but the yield is relatively low.
As can be seen from the above synthesis methods, the prior art has a great disadvantage, such as the use of a large amount of inorganic acid to generate a large amount of waste, or high cost, or the use of a metal catalyst, which is unfavorable for the mass production of 2-methylquinoline, and a synthesis method with environmental protection and higher efficiency is needed.
Disclosure of Invention
In order to solve the technical problems, the invention takes aromatic amine and paraldehyde as raw materials, and synthesizes 2-methylquinoline under milder conditions through cyclization reaction under the action of an iodine-containing compound as a catalyst, an oxidant and a solvent. The method does not need a transition metal catalyst, and provides an environment-friendly high-efficiency new path for synthesizing the compounds. The method also has the advantages of simple reaction system, mild condition, wide raw material source, low price, high yield, easy expansion of application and the like.
In order to achieve the above purpose, the invention provides a method for synthesizing 2-methylquinoline by taking paraldehyde as a raw material, which comprises the following steps: aniline shown in formula 1 and paraldehyde shown in formula 2 are taken as substrates, then a catalyst, an oxidant and a solvent are added for mixing, the mixture is reacted for 1 to 48 hours at 50 to 140 ℃, and the product is purified to obtain 2-methylquinoline shown in formula 3;
the catalyst is an iodine-containing compound or elemental iodine;
。
preferably, the iodine-containing compound is one of potassium iodide, sodium iodide, ammonium iodide, iodine chloride, iodine bromide and succinimide.
Preferably, the oxidizing agent is one of oxygen and air.
Preferably, the solvent is one of ethylene glycol, diethylene glycol, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, polyethylene glycol 400, toluene, o-xylene, m-xylene, p-xylene, and N, N-methyl formamide (DMF).
Preferably, the molar ratio of the aniline to the iodine-containing compound to the paraldehyde is 1:0.05-0.5:7-56.
Preferably, the volume ratio of the paraldehyde to the solvent is 1:0-0.5.
The reaction mechanism of the invention is as follows:
the reaction mechanism of the invention is shown in figure 1, the iodine-containing compound of the catalyst generates iodine free radical I.under the heating condition, the latter reacts with aniline to generate free radical A, the paraldehyde generates acetaldehyde under the heating condition, the acetaldehyde is isomerized to generate vinyl alcohol, the free radical A is added to the vinyl alcohol to generate free radical B, the latter is isomerized to generate free radical C, the free radical C is added to the vinyl alcohol to generate free radical D, the free radical D is added in the molecule to generate free radical E, the latter generates intermediate F under the action of oxidant such as oxygen, the latter is dehydrated to generate intermediate G, and the intermediate G is structurally interconverted to obtain the product 2-methylquinoline (III).
Compared with the prior art, the invention has the following beneficial effects:
(1) The invention provides a synthetic method for efficiently generating 2-methylquinoline by aniline and paraldehyde in one pot under the combined action of a catalyst, an oxidant and a solvent without transition metal catalysis.
(2) According to the invention, aromatic amine and paraldehyde are used as starting materials, 2-methylquinoline is efficiently synthesized under the optimal reaction condition, and the reaction yield can reach 80%. The method has the characteristics of mild reaction conditions, simple and easily obtained raw materials, high reaction efficiency and the like.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are needed in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a diagram of the reaction mechanism for synthesizing 2-methylquinoline according to the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the product 2-methylquinoline of example 1;
FIG. 3 is a nuclear magnetic resonance spectrum of the product 2-methylquinoline of example 1.
Detailed Description
In order to make the technical problems, technical solutions and advantages to be solved more apparent, the following detailed description will be given with reference to the accompanying drawings and specific embodiments.
The following examples are illustrative of the invention and are not intended to limit the scope of the invention. Modifications and substitutions to methods, procedures, or conditions of the present invention without departing from the spirit and nature of the invention are intended to be within the scope of the present invention.
The technical means used in the examples are conventional means well known to those skilled in the art unless otherwise indicated; the reagents used in the examples were all commercially available unless otherwise specified.
Examples 1-38, 2-methylquinoline was prepared.
S1, adding reactants, a catalyst, an oxidant and a solvent into a reactor, wherein the reactants are aniline and paraldehyde;
s2, fully mixing the reactant in the step S1 with a catalyst, an oxidant and a solvent, and then heating a reactor to enable the reactant to react to obtain a mixture;
s3, purifying the mixture in the step S2: evaporating the mixture solvent to dryness, and separating by column chromatography with silica gel as adsorbent to obtain 2-methylquinoline.
The molar ratio, volume ratio and reaction conditions of the iodine-containing compound and the oxidant in the preparation process are shown in table 1:
TABLE 1 catalysts, oxidants, solvents, molar ratios, volume ratios, reaction conditions and yields for examples 1-38
，
，
，
Molar ratio is the molar ratio of aniline, catalyst, and paraldehyde;
the volume ratio # is the volume ratio of the paraldehyde to the solvent.
Examining the yields of the reaction products of the reactions of examples 1-38 and performing nuclear magnetic resonance characterization, wherein the yields are shown in table 1, the catalyst is elemental iodine, the oxidant is oxygen, and the solvent is toluene; the molar ratio of aniline to elemental iodine to paraldehyde is 1:0.05:36, the volume ratio of paraldehyde to solvent is 2:1, the reaction condition is 110 ℃, and the highest yield of 2-methylquinoline is 80% when the reaction time is 16 hours;
the nuclear magnetic hydrogen spectrum of the product of example 1 is shown in figure 2;
the nuclear magnetic carbon spectrum of the product of example 1 is shown in FIG. 3;
example 1 nuclear magnetic data for product 2-methylquinoline:
1 H NMR (400MHz，CDCl3 , ppm) δ 8.03 (t, J = 8.0 Hz, 2H), 7.77 (d, J = 8.0 Hz, 1H), 7.68 (t, J = 8.0 Hz, 1H), 7.48 (t, J = 8.0 Hz, 1H), 7.29 (d, J = 8.0 Hz, 1H), 2.75 (s, 3H)；13C NMR (100MHz，CDCl3, ppm ) δ 159.0, 147.8, 136.2, 129.4, 128.6, 127.5, 126.5, 125.6, 122.0, 25.4。
Claims (6)
1. the method for synthesizing the 2-methylquinoline by taking the paraldehyde as the raw material is characterized by comprising the following steps of: aniline shown in formula 1 and paraldehyde shown in formula 2 are taken as substrates, then a catalyst, an oxidant and a solvent are added for mixing, the mixture is reacted for 1 to 48 hours at 50 to 140 ℃, and the product is purified to obtain 2-methylquinoline shown in formula 3;
the catalyst is an iodine-containing compound or elemental iodine;
。
2. the method of claim 1, wherein the iodine-containing compound is one of potassium iodide, sodium iodide, ammonium iodide, iodine chloride, iodine bromide, and succinimide.
3. The method of claim 1, wherein the oxidizing agent is one of oxygen and air.
4. The method of claim 1, wherein the solvent is one of ethylene glycol, diethylene glycol, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, polyethylene glycol 400, toluene, o-xylene, m-xylene, p-xylene, N-methyl formamide.
5. The method according to claim 1, wherein the molar ratio of aniline, iodine-containing compound, and paraldehyde is 1:0.05-0.5:7-56.
6. The method according to claim 1, wherein the volume ratio of the paraldehyde to the solvent is 1:0-0.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311313247.4A CN117069654A (en) | 2023-10-11 | 2023-10-11 | Method for synthesizing 2-methylquinoline by taking paraldehyde as raw material |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311313247.4A CN117069654A (en) | 2023-10-11 | 2023-10-11 | Method for synthesizing 2-methylquinoline by taking paraldehyde as raw material |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005035894A (en) * | 2003-07-15 | 2005-02-10 | Koei Chem Co Ltd | Method for producing quinoline compound |
| CN101429157A (en) * | 2008-06-05 | 2009-05-13 | 先尼科化工（上海）有限公司 | Process for producing 2-methyl-8-nitryl quinoline |
| CN101805287A (en) * | 2010-04-01 | 2010-08-18 | 浙江工业大学 | Method for one-pot liquid phase synthesis of quinoline and derivative thereof |
| CN102464613A (en) * | 2010-11-10 | 2012-05-23 | 中国石油大学(北京) | Synthetic method of quinoline derivative |
| CN102898366A (en) * | 2012-03-30 | 2013-01-30 | 浙江工业大学 | Method for one-step preparation of 2-methylquinoline |
| CN114292231A (en) * | 2021-12-17 | 2022-04-08 | 江苏广域化学有限公司 | 2-methyl-8-substituent-quinoline and preparation method thereof |
-
2023
- 2023-10-11 CN CN202311313247.4A patent/CN117069654A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005035894A (en) * | 2003-07-15 | 2005-02-10 | Koei Chem Co Ltd | Method for producing quinoline compound |
| CN101429157A (en) * | 2008-06-05 | 2009-05-13 | 先尼科化工（上海）有限公司 | Process for producing 2-methyl-8-nitryl quinoline |
| CN101805287A (en) * | 2010-04-01 | 2010-08-18 | 浙江工业大学 | Method for one-pot liquid phase synthesis of quinoline and derivative thereof |
| CN102464613A (en) * | 2010-11-10 | 2012-05-23 | 中国石油大学(北京) | Synthetic method of quinoline derivative |
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| CN114292231A (en) * | 2021-12-17 | 2022-04-08 | 江苏广域化学有限公司 | 2-methyl-8-substituent-quinoline and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| TAKEYUKI IGARASHI ET AL.: "One-pot Synthesis of Substituted Quinolines by Iridium-catalyzed Three-component Coupling Reaction", CHEMISTRY LETTERS, vol. 34, no. 1, pages 106 - 107 * |
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