CN102766082A - Novel method for synthesizing indole-3-carbinol - Google Patents
Novel method for synthesizing indole-3-carbinol Download PDFInfo
- Publication number
- CN102766082A CN102766082A CN2012102756404A CN201210275640A CN102766082A CN 102766082 A CN102766082 A CN 102766082A CN 2012102756404 A CN2012102756404 A CN 2012102756404A CN 201210275640 A CN201210275640 A CN 201210275640A CN 102766082 A CN102766082 A CN 102766082A
- Authority
- CN
- China
- Prior art keywords
- indole
- carbinol
- novel method
- methyl alcohol
- present
- 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
- 238000000034 method Methods 0.000 title claims abstract description 16
- IVYPNXXAYMYVSP-UHFFFAOYSA-N Indole-3-carbinol Natural products C1=CC=C2C(CO)=CNC2=C1 IVYPNXXAYMYVSP-UHFFFAOYSA-N 0.000 title abstract description 5
- 235000002279 indole-3-carbinol Nutrition 0.000 title abstract description 4
- RUMVKBSXRDGBGO-UHFFFAOYSA-N indole-3-carbinol Chemical compound C1=CC=C[C]2C(CO)=CN=C21 RUMVKBSXRDGBGO-UHFFFAOYSA-N 0.000 title abstract 3
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 6
- 239000011591 potassium Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 150000002475 indoles Chemical class 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000012043 crude product Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000012265 solid product Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 229940071559 trioxin Drugs 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Abstract
The invention provides a novel method for synthesizing indole-3-carbinol. The new method comprises the following steps: 1, accurately preparing 0.2mol of indole-3-formaldehyde, 200ml of ethanol with concentration being 99% and 0.2mol of potassium borohydride and reacting at a room temperature for 3h; 2, reducing pressure to minus 0.8mpa and concentrating; and adding 500ml of water and separating out a solid product which is the crude product of indole-3-carbinol. According to the new method, since medicinal alcohol is used as a solvent, the problem benzene residues exceed the standard is solved and the cost is reduced.
Description
Technical field
The invention belongs to technical field of chemistry, relate to a kind of novel method of synthesis of indole 3 methyl alcohol.
Background technology
Present industrial synthesis technique is according to Wei Er David Smail (Vilsmeier.A.) reaction synthesis of indole-3-formaldehyde, to be reduced into indole-3-carbinol then.The Vilsmeier reaction is widely used as the process for hydroformylation of aromatic compound (substituted arene, arylamine, phenol and phenolic ether etc.) and heterogeneous ring compound (pyrroles, indoles, pyridine etc.).In the presence of POCl3, the intermediate that condensation generates is hydrolyzed into corresponding aldehydes in acid solution with substituted formamides (DMF or MFA), aromatic series and heterogeneous ring compound, during the reduction indole-3-formaldehyde, usefulness be toluene water potassium borohydride reduction system.
To be that benzene is residual exceed standard the prior art shortcoming, and it is higher relatively to do solvent cost with toluene.
Summary of the invention
In order to overcome the defective that exists in the prior art, thoroughly solve the dissolvent residual problem of product, the present invention provides a kind of novel method of synthesis of indole 3 methyl alcohol, with the product that present method is made, does not have benzene residual residual with toluene.
Its technical scheme is following:
A kind of novel method of synthesis of indole 3 methyl alcohol may further comprise the steps:
1) accurately take by weighing indoles 3 formaldehyde 0.2mol, concentration is 200 milliliters of 99% ethanol, POTASSIUM BOROHYDRIDE 97MIN 0.2mol, room temperature reaction 3 hours;
2) be decompressed to-0.8mpa, concentrate;
3) add 500 milliliters in water, separate out solid, be indoles 3 methyl alcohol bullions.
Principle of the present invention is: indoles trioxin+POTASSIUM BOROHYDRIDE 97MIN+ethanol → indoles 3 methyl alcohol
Beneficial effect of the present invention:
Catalyzer Heat stability is good of the present invention, little to equipment corrosion, reaction is after filter, and catalyzer can separate with product, and the catalyzer repeat performance is good, can realize cleaner production.
Advantage of the present invention: the novel method of synthesis of indole 3 methyl alcohol of the present invention, the employing medical alcohol is a solvent, has solved the residual problem that exceeds standard of benzene, and has reduced cost.
Embodiment
Below in conjunction with specific embodiment method of the present invention is done explanation in further detail.
A kind of novel method of synthesis of indole 3 methyl alcohol may further comprise the steps:
1) accurately take by weighing indoles 3 formaldehyde 0.2mol, concentration is 200 milliliters of 99% ethanol, POTASSIUM BOROHYDRIDE 97MIN 0.2mol, room temperature reaction 3 hours;
2) be decompressed to-0.8mpa, concentrate;
3) add 500 milliliters in water, separate out solid, be indoles 3 methyl alcohol bullions.
The above; Be merely the preferable embodiment of the present invention; Protection scope of the present invention is not limited thereto; Any technician who is familiar with the present technique field is in the technical scope that the present invention discloses, and the simple change of the technical scheme that obtains or equivalence replacement all fall in protection scope of the present invention with may be obvious that.
Claims (1)
1. the novel method of synthesis of indole 3 methyl alcohol is characterized in that, may further comprise the steps:
1) accurately take by weighing indoles 3 formaldehyde 0.2mol, concentration is 200 milliliters of 99% ethanol, POTASSIUM BOROHYDRIDE 97MIN 0.2mol, room temperature reaction 3 hours;
2) be decompressed to-0.8mpa, concentrate;
3) add 500 milliliters in water, separate out solid, be indoles 3 methyl alcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012102756404A CN102766082A (en) | 2012-08-03 | 2012-08-03 | Novel method for synthesizing indole-3-carbinol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012102756404A CN102766082A (en) | 2012-08-03 | 2012-08-03 | Novel method for synthesizing indole-3-carbinol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102766082A true CN102766082A (en) | 2012-11-07 |
Family
ID=47093693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012102756404A Pending CN102766082A (en) | 2012-08-03 | 2012-08-03 | Novel method for synthesizing indole-3-carbinol |
Country Status (1)
| Country | Link |
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| CN (1) | CN102766082A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103232377A (en) * | 2013-05-14 | 2013-08-07 | 张家港威胜生物医药有限公司 | Synthesis process of natural component indole-3-methanol for preventing tumor |
| CN113845463A (en) * | 2021-11-15 | 2021-12-28 | 西安久中生物科技有限公司 | Environment-friendly preparation process of indole-3-methanol |
| RU2772604C1 (en) * | 2021-07-06 | 2022-05-23 | Всеволод Иванович Киселев | Method for producing indole-3-carbinol (variants) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1225882B1 (en) * | 1999-08-30 | 2007-10-17 | Vanderbilt University | Selective cox-2 inhibitory novel esters from indolealkanols and novel amides from indolealkylamines |
| CN101921223A (en) * | 2010-05-07 | 2010-12-22 | 南京锐马精细化工有限公司 | Synthesis method of indole-3-methanol |
| CN102167679A (en) * | 2011-01-21 | 2011-08-31 | 东南大学 | Method of synthesizing styryl indole compounds |
-
2012
- 2012-08-03 CN CN2012102756404A patent/CN102766082A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1225882B1 (en) * | 1999-08-30 | 2007-10-17 | Vanderbilt University | Selective cox-2 inhibitory novel esters from indolealkanols and novel amides from indolealkylamines |
| CN101921223A (en) * | 2010-05-07 | 2010-12-22 | 南京锐马精细化工有限公司 | Synthesis method of indole-3-methanol |
| CN102167679A (en) * | 2011-01-21 | 2011-08-31 | 东南大学 | Method of synthesizing styryl indole compounds |
Non-Patent Citations (2)
| Title |
|---|
| 周佳栋，等: "N-取代吲哚-3-甲醇的合成", 《精细化工》 * |
| 沈新安: "吲哚-3-甲醇的合成", 《现代化工》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103232377A (en) * | 2013-05-14 | 2013-08-07 | 张家港威胜生物医药有限公司 | Synthesis process of natural component indole-3-methanol for preventing tumor |
| RU2772604C1 (en) * | 2021-07-06 | 2022-05-23 | Всеволод Иванович Киселев | Method for producing indole-3-carbinol (variants) |
| CN113845463A (en) * | 2021-11-15 | 2021-12-28 | 西安久中生物科技有限公司 | Environment-friendly preparation process of indole-3-methanol |
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Application publication date: 20121107 |