CN110642770B - Preparation method of 5-methoxyindole - Google Patents
Preparation method of 5-methoxyindole Download PDFInfo
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- CN110642770B CN110642770B CN201910880918.2A CN201910880918A CN110642770B CN 110642770 B CN110642770 B CN 110642770B CN 201910880918 A CN201910880918 A CN 201910880918A CN 110642770 B CN110642770 B CN 110642770B
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- bromoindole
- methoxyindole
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- sodium methoxide
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- DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical compound COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- VXWVFZFZYXOBTA-UHFFFAOYSA-N 5-bromo-1h-indole Chemical compound BrC1=CC=C2NC=CC2=C1 VXWVFZFZYXOBTA-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 238000001816 cooling Methods 0.000 claims abstract description 11
- 150000004699 copper complex Chemical class 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims abstract description 6
- 239000013078 crystal Substances 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims abstract description 3
- 239000000706 filtrate Substances 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 230000035484 reaction time Effects 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 9
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical group CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 3
- 229940045803 cuprous chloride Drugs 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- GLVGKBXXSZDILY-UHFFFAOYSA-N BrC=1C=C2C=CNC2=CC1.COC=1C=C2C=CNC2=CC1 Chemical compound BrC=1C=C2C=CNC2=CC1.COC=1C=C2C=CNC2=CC1 GLVGKBXXSZDILY-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 238000003760 magnetic stirring Methods 0.000 description 8
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 7
- 238000005070 sampling Methods 0.000 description 7
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 4
- IKCZUPRWPVLSLF-UHFFFAOYSA-N 2-methoxy-1h-indole Chemical compound C1=CC=C2NC(OC)=CC2=C1 IKCZUPRWPVLSLF-UHFFFAOYSA-N 0.000 description 3
- 150000002475 indoles Chemical class 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000027288 circadian rhythm Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- OXZOLXJZTSUDOM-UHFFFAOYSA-N fluoro 2,2,2-trifluoroacetate Chemical compound FOC(=O)C(F)(F)F OXZOLXJZTSUDOM-UHFFFAOYSA-N 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 1
- 229960003987 melatonin Drugs 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Classifications
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- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
- B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Indole Compounds (AREA)
Abstract
The invention discloses a preparation method of 5-methoxyindole, which comprises the following steps: s1, mixing 5-bromoindole and a methanol solution of sodium methoxide uniformly, adding a catalyst for reaction, and controlling the reaction temperature to be 80-120 ℃ and the reaction time to be 5-10 hours; the catalyst comprises a nitrogen-containing heterocycle and a monovalent copper complex, and the mass ratio of the catalyst to the 5-bromoindole is (0.05-0.1): 1; the molar ratio of the sodium methoxide to the 5-bromoindole is 1.3-2: 1; s2, cooling the obtained product, filtering, distilling the obtained filtrate under reduced pressure to recover methanol, extracting, recrystallizing, and drying the separated crystal to obtain 5-methoxyindole; the invention adopts a new catalyst system, reduces the cost, has high reaction selectivity, and has the conversion rate of synthesizing the 5-methoxyindole 5-bromoindole by one step of over 95 percent.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a preparation method of 5-methoxyindole.
Background
5-methoxyindole is an important medical intermediate and an important raw material for producing medicaments for preventing and treating cardiovascular diseases, neurological diseases and tumors and enhancing immunity. One of the important applications is the synthesis of tryptamine compounds, wherein the melatonin and the derivatives thereof are very effective in regulating the circadian rhythm and the sleep, resisting tumors and the like.
The application number is 'CN201711026288. X', the name is '5-methoxyindole production method based on porous alumina composite catalyst adsorbing tetrafluoroacetic acid', and the method discloses a process for synthesizing 5-methoxyindole from 5-bromoindole, wherein cuprous iodide is used as a catalyst, 5-bromoindole and sodium methoxide are synthesized in DMF, the yield is about 80%, the cuprous iodide is very high in price and large in dosage, and the cost of the 5-methoxyindole synthesized by the process is extremely high; and the yield is low, and the waste causes certain pollution to the environment.
How to develop a new catalyst for preparing 5-methoxyindole so as to reduce cost and improve environmental pollution becomes a technical problem to be solved urgently.
Disclosure of Invention
The invention aims to overcome the defects of the prior art, and provides a preparation method of 5-methoxyindole, which adopts a new catalyst system, reduces the cost, has high reaction selectivity, ensures that the conversion rate of 5-methoxyindole 5-bromoindole synthesized in one step is more than 95 percent, ensures that the selectivity of 5-methoxyindole is more than 90 percent, and has high environmental protection and economy.
The invention is realized by the following steps:
the invention aims to provide a preparation method of 5-methoxyindole, which comprises the following steps:
s1, mixing 5-bromoindole and a methanol solution of sodium methoxide uniformly, adding a catalyst for reaction, and controlling the reaction temperature to be 80-120 ℃ and the reaction time to be 5-10 hours; the catalyst comprises a nitrogen-containing heterocycle and a monovalent copper complex, and the mass ratio of the catalyst to the 5-bromoindole is (0.05-0.1): 1; the molar ratio of the sodium methoxide to the 5-bromoindole is 1.3-2: 1;
s2, cooling the obtained product, filtering, recovering methanol from the obtained filtrate, extracting, recrystallizing, and drying the separated crystal to obtain the 5-methoxyindole.
Preferably, the concentration of sodium methoxide in the methanol solution of sodium methoxide is 25-35%.
Preferably, the nitrogen-containing heterocycle in the catalyst comprises at least one of phenanthroline, methylimidazole and bipyridine.
Preferably, the monovalent copper complex in the catalyst comprises one of cuprous bromide and cuprous chloride. Preferably, the mass ratio of the nitrogen-containing heterocycle to the monovalent copper complex in the catalyst is 0.8-1.5: 0.2 to 0.6.
Preferably, the reaction temperature is 90-110 ℃.
Compared with the prior art, the invention has the following advantages and effects:
1. the invention provides a preparation method of 5-methoxyindole, which takes 5-bromoindole and sodium methoxide as raw materials, takes a nitrogen-containing heterocycle and a cuprous complex as a catalyst, and has the conversion rate of synthesizing the 5-methoxyindole 5-bromoindole by one step of over 95 percent and the selectivity of the 5-methoxyindole of over 90 percent.
2. The preparation method of 5-methoxyindole provided by the invention adopts a new catalyst system, reduces the cost, has high reaction selectivity, and has high environmental protection property and economy.
Drawings
FIG. 1 is a chromatogram of 5-methoxyindole prepared in example 1 of the present invention.
Detailed Description
Example 1
36 g of 30% sodium methoxide in methanol (0.2 mol of sodium methoxide), 19.6 g of 5-bromoindole (0.1 mol of molecular weight 196) and 1.5 g of phenanthroline and 0.4 g of cuprous bromide were added to a 200ml reaction vessel at room temperature, magnetic stirring was started, and the temperature was raised to 120 ℃ to carry out the reaction for 10 hours. And cooling to room temperature, and sampling, detecting and analyzing to obtain a result that the conversion rate of the 5-bromoindole is 97.1% and the selectivity of the 5-methoxyindole is 95.2%.
And (3) post-treatment: after the solvent is removed by rotary evaporation from the reaction solution of example 1, the reaction solution is extracted by toluene, then the toluene is removed by rotary evaporation, and the product is recrystallized by petroleum ether to obtain 12.1 g of product with the purity of 96.1 percent, and the product chromatogram is shown in figure 1. The retention time of each peak in the chromatogram is shown in Table 1 below.
TABLE 1
| Peak(s) | Residence time | Substance(s) | Peak(s) | Residence time | Substance(s) |
| 1 | 1.86 | Methanol | 6 | 24.31 | 5-methoxyindole |
| 2 | 2.07 | Ethanol | 7 | 25.57 | 5-bromoindoles |
| 3 | 4.59 | Toluene | 8 | 25.72 | |
| 4 | 5.73 | Xylene | 9 | 27.78 | Unknown indoles |
| 5 | 22.52 | Unknown indoles |
Example 2
At room temperature, 35 g of 30% sodium methoxide in methanol (0.194 mol of sodium methoxide), 19.6 g of 5-bromoindole (0.1 mol) and 1 g of phenanthroline, 0.2 g of cuprous bromide were added to a 200ml reaction vessel, magnetic stirring was started, and the temperature was raised to 120 ℃ to carry out a reaction for 7 hours. And cooling to room temperature, and sampling, detecting and analyzing to obtain a result that the conversion rate of the 5-bromoindole is 95.6% and the selectivity of the 5-methoxyindole is 94.4%.
Example 3
35 g of 30% sodium methoxide in methanol (sodium methoxide 0.194 mol: 5410.476 g), 19.6 g of 5-bromoindole (0.1 mol.) and 1.5 g of bipyridine, 0.4 g of cuprous bromide were put into a 200ml reaction vessel at room temperature, and magnetic stirring was started, and the temperature was raised to 100 ℃ to carry out a reaction for 8 hours. And cooling to room temperature, and sampling, detecting and analyzing to obtain a result that the conversion rate of the 5-bromoindole is 96.8% and the selectivity of the methoxyindole is 93.5%.
Example 4
42 g of 25% sodium methoxide in methanol (0.194 mol of sodium methoxide), 19.6 g of 5-bromoindole (0.1 mol) and 1.5 g of methylimidazole, 0.4 g of cuprous bromide were placed in a 200ml reaction vessel at room temperature, and magnetic stirring was started, and the temperature was raised to 120 ℃ to carry out a reaction for 10 hours. And cooling to room temperature, and sampling, detecting and analyzing to obtain a result that the conversion rate of the 5-bromoindole is 95.1% and the selectivity of the methoxyindole is 92.4%.
Example 5
26 g of 35% sodium methoxide in methanol (0.167 mol of sodium methoxide), 19.6 g of 5-bromoindole (0.1 mol) and 1 g of phenanthroline, 0.5 g of bipyridine and 0.4 g of cuprous bromide were added to a 200ml reaction vessel at room temperature, magnetic stirring was started, and the temperature was raised to 120 ℃ to carry out the reaction for 10 hours. And (3) cooling, and detecting and analyzing to obtain a result that the conversion rate of the 5-bromoindole is 97.3% and the selectivity of the 5-methoxyindole is 94.7%.
Example 6
24 g of 30% sodium methoxide in methanol (sodium methoxide 0.133), 10 g of methanol, 19.6 g of 5-bromoindole (0.1 mol) and 0.4 g of phenanthroline, 0.4 g of bipyridine and 0.2 g of cuprous chloride are added to a 200ml reaction vessel at room temperature, magnetic stirring is started, and the temperature is raised to 100 ℃ for reaction for 9 hours. And cooling to room temperature, and sampling, detecting and analyzing to obtain a result that the conversion rate of the 5-bromoindole is 96.7 percent and the selectivity of the methoxyindole is 92.1 percent.
Example 7
30 g of 30% sodium methoxide in methanol (sodium methoxide 0.167), 19.6 g of 5-bromoindole (0.1 mol) and 1 g of phenanthroline, 0.2 g of methylimidazole and 0,3 g of cuprous bromide are added to a 200ml reaction kettle at room temperature, magnetic stirring is started, and the temperature is raised to 110 ℃ for reaction for 10 hours. And cooling to room temperature, and sampling, detecting and analyzing to obtain a result that the conversion rate of the 5-bromoindole is 96.4% and the selectivity of the 5-methoxyindole is 91%.
Example 8
30 g of 30% sodium methoxide in methanol (0.167 mol of sodium methoxide), 19.6 g of 5-bromoindole (0.1 mol) and 1.2 g of phenanthroline and 0.6 g of cuprous bromide were added to a 200ml reaction vessel at room temperature, magnetic stirring was started, and the temperature was raised to 80 ℃ to carry out the reaction for 10 hours. And cooling to room temperature, and sampling, detecting and analyzing to obtain a result that the conversion rate of the 5-bromoindole is 95.1% and the selectivity of the 5-methoxyindole is more than 97.5%.
The invention is not to be considered as limited to the particular embodiments shown, but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (6)
1. A preparation method of 5-methoxyindole is characterized by comprising the following steps:
s1, mixing 5-bromoindole and a methanol solution of sodium methoxide uniformly, adding a catalyst for reaction, and controlling the reaction temperature to be 80-120 ℃ and the reaction time to be 5-10 hours; the catalyst comprises a nitrogen-containing heterocycle and a monovalent copper complex, and the mass ratio of the catalyst to the 5-bromoindole is (0.05-0.1): 1; the molar ratio of the sodium methoxide to the 5-bromoindole is 1.3-2: 1;
s2, cooling the obtained product, filtering, recovering methanol from the obtained filtrate, extracting, recrystallizing, and drying the separated crystal to obtain 5-methoxyindole;
the univalent copper complex in the catalyst comprises cuprous bromide or cuprous chloride, and the nitrogen-containing heterocycle in the catalyst is methylimidazole.
2. The method according to claim 1, wherein the concentration of sodium methoxide in the methanol solution of sodium methoxide is 25 to 35%.
3. The method according to claim 1, wherein the mass ratio of the nitrogen-containing heterocycle to the monovalent copper complex in the catalyst is 0.8 to 1.5: 0.2 to 0.6.
4. The method according to claim 1, wherein the reaction temperature is 90 to 110 ℃.
5. The method of claim 1, wherein the solvent used for the extraction is toluene.
6. The method according to claim 1, wherein the recrystallization uses petroleum ether.
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