CN103664733B - A kind of preparation method of indoline - Google Patents
A kind of preparation method of indoline Download PDFInfo
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- CN103664733B CN103664733B CN201310660992.6A CN201310660992A CN103664733B CN 103664733 B CN103664733 B CN 103664733B CN 201310660992 A CN201310660992 A CN 201310660992A CN 103664733 B CN103664733 B CN 103664733B
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- Prior art keywords
- indoline
- pressure
- indoles
- preparation
- catalyzer
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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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention discloses a kind of preparation method of indoline, comprising the following steps (1) joins in autoclave by indoles and catalyzer, with air in nitrogen replacement still, be warming up to 150 ~ 200 DEG C, pass into hydrogen, and keep the pressure of 5.0 ~ 9.0Mpa, react when not declining to pressure and stop heating; (2) be cooled to less than 40 DEG C, filter, filtrate is carried out rectification under vacuum and is obtained indoline.The inventive method is simple, and yield is high, take indoles as raw material, and Raney's nickel is that catalyzer carries out hydrogenation reaction, and the purity that rectifying obtains indoline is high.
Description
Technical field
The present invention relates to heterogeneous ring compound technical field.
Background technology
Indoline of many uses, is usually used in pharmacy or the derived product for the synthesis of indoles, and indoline-like dyestuff is used as quick dose of solid-state dye sensitized solar cell.In prior art, indoline generally adopts following method to prepare, and is obtained by adjacent aminoethylbenzene catalysis, and adjacent aminoethylbenzene is in nitrogen gas stream, and under aluminum nitrate (or aluminium sesquioxide) exists, about 550 DEG C dehydrocyclizations, obtain indoline through underpressure distillation.The feature of this method is that turnout is large, is applicable to continuous seepage, and shortcoming is that method is complicated, and yield is low, and product purity is low, and impurity is high.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of preparation method of indoline, and the inventive method is simple, and yield is high, and the purity obtaining indoline is high.
For solving the problems of the technologies described above, the technical solution used in the present invention is: a kind of preparation method of indoline, comprising the following steps (1) joins in autoclave by indoles and catalyzer, with air in nitrogen replacement still, be warming up to 150 ~ 200 DEG C, pass into hydrogen, and keep the pressure of 5.0 ~ 9.0Mpa, react when not declining to pressure and stop heating;
(2) be cooled to less than 40 DEG C, filter, filtrate is carried out rectification under vacuum and is obtained indoline.
Catalyzer in step (1) is Raney's nickel catalyst.
In step (1), the mass ratio of indoles and catalyzer is 10:0.6 ~ 1.2.
In step (2), the pressure of rectification under vacuum is-0.09MPa.
The beneficial effect adopting technique scheme to produce is: the inventive method is simple, and yield is high, and yield can reach more than 90%, take indoles as raw material, and Raney's nickel is that catalyzer carries out hydrogenation reaction, and the purity that rectifying obtains indoline can reach 99.5%.
Embodiment
Embodiment 1
A kind of preparation method of indoline, comprising the following steps (1) joins in the autoclave of band whipping appts by the indoles of 500 gram 95% and 50g Raney's nickel catalyst, with air in nitrogen replacement still, be warming up to 180 DEG C, pass into hydrogen, and keep the pressure of 7Mpa, react when not declining to pressure and stop heating;
(2) be cooled to less than 40 DEG C, filter, filtrate is carried out rectification under vacuum and is obtained indoline, and pressure is-0.09Mpa, and product purity is 99.5%, and yield is 90%.
Embodiment 2
A kind of preparation method of indoline, comprising the following steps (1) joins in the autoclave of band whipping appts by the indoles of 500 gram 95% and 30g Raney's nickel catalyst, with air in nitrogen replacement still, be warming up to 200 DEG C, pass into hydrogen, and keep the pressure of 5Mpa, react when not declining to pressure and stop heating;
(2) be cooled to less than 40 DEG C, filter, filtrate is carried out rectification under vacuum and is obtained indoline, and pressure is-0.09Mpa, and product purity is 99.6%, and yield is 88%.
Embodiment 3
A kind of preparation method of indoline, comprising the following steps (1) joins in the autoclave of band whipping appts by the indoles of 500 gram 95% and 60g Raney's nickel catalyst, with air in nitrogen replacement still, be warming up to 150 DEG C, pass into hydrogen, and keep the pressure of 9Mpa, react when not declining to pressure and stop heating;
(2) be cooled to less than 40 DEG C, filter, filtrate is carried out rectification under vacuum and is obtained indoline, and pressure is-0.09Mpa, and product purity is 99.7%, and yield is 89%.
Embodiment 4
A kind of preparation method of indoline, comprising the following steps (1) joins in the autoclave of band whipping appts by the indoles of 5000 gram 95% and 500g Raney's nickel catalyst, with air in nitrogen replacement still, be warming up to 180 DEG C, pass into hydrogen, and keep the pressure of 7Mpa, react when not declining to pressure and stop heating;
(2) be cooled to less than 40 DEG C, filter, filtrate is carried out rectification under vacuum and is obtained indoline, and pressure is-0.09Mpa, and product purity is 99.5%, and yield is 90%.
Embodiment 5
A kind of preparation method of indoline, comprising the following steps (1) joins in the autoclave of band whipping appts by the indoles of 500 kilogram 95% and 30Kg Raney's nickel catalyst, with air in nitrogen replacement still, be warming up to 200 DEG C, pass into hydrogen, and keep the pressure of 5Mpa, react when not declining to pressure and stop heating;
(2) be cooled to less than 40 DEG C, filter, filtrate is carried out rectification under vacuum and is obtained indoline, and pressure is-0.09Mpa, and product purity is 99.6%, and yield is 87%.
Embodiment 6
A kind of preparation method of indoline, comprising the following steps (1) joins in the autoclave of band whipping appts by the indoles of 5000 kilogram 95% and 60Kg Raney's nickel catalyst, with air in nitrogen replacement still, be warming up to 150 DEG C, pass into hydrogen, and keep the pressure of 9Mpa, react when not declining to pressure and stop heating;
(2) be cooled to less than 40 DEG C, filter, filtrate is carried out rectification under vacuum and is obtained indoline, and pressure is-0.09Mpa, and product purity is 99.7%, and yield is 89%.
Claims (2)
1. the preparation method of an indoline, it is characterized in that: comprise the following steps (1) and indoles and catalyzer are joined in autoclave, with air in nitrogen replacement still, be warming up to 150 ~ 200 DEG C, pass into hydrogen, and keep the pressure of 5.0 ~ 9.0Mpa, react when not declining to pressure and stop heating;
(2) be cooled to less than 40 DEG C, filter, filtrate is carried out rectification under vacuum and is obtained indoline;
Catalyzer in step (1) is Raney's nickel catalyst;
In step (1), the mass ratio of indoles and catalyzer is 10:0.6 ~ 1.2.
2. the preparation method of indoline as claimed in claim 1, is characterized in that: in step (2), the pressure of rectification under vacuum is-0.09MPa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310660992.6A CN103664733B (en) | 2013-12-10 | 2013-12-10 | A kind of preparation method of indoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310660992.6A CN103664733B (en) | 2013-12-10 | 2013-12-10 | A kind of preparation method of indoline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103664733A CN103664733A (en) | 2014-03-26 |
| CN103664733B true CN103664733B (en) | 2016-04-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201310660992.6A Active CN103664733B (en) | 2013-12-10 | 2013-12-10 | A kind of preparation method of indoline |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107021968B (en) * | 2017-05-25 | 2018-12-07 | 陕西师范大学 | The method of the polysubstituted organic photochemical catalyst catalyzing indole quinoline class compound oxidation dehydrogenation synthesis of indole class compound of BODIPY |
| CN112300048A (en) * | 2020-10-23 | 2021-02-02 | 河北中化鑫宝化工科技有限公司 | Preparation method of indoline with low cost |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4376205A (en) * | 1981-04-15 | 1983-03-08 | Mitsui Toatsu Chemicals, Inc. | Process for the preparation of indoles from anilines and ethanolamines |
| CN1342143A (en) * | 1999-03-04 | 2002-03-27 | 美国家用产品公司 | N-substituted indolines as estrogenic agents |
| CN101652346A (en) * | 2007-02-01 | 2010-02-17 | 约瑟夫·傅立叶大学 | Novel indole derivatives, process for their preparation and use, especially as antibacterial agents |
| WO2010051374A1 (en) * | 2008-10-31 | 2010-05-06 | Pain Therapeutics, Inc. | Analgesic that binds filamin a |
-
2013
- 2013-12-10 CN CN201310660992.6A patent/CN103664733B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4376205A (en) * | 1981-04-15 | 1983-03-08 | Mitsui Toatsu Chemicals, Inc. | Process for the preparation of indoles from anilines and ethanolamines |
| CN1342143A (en) * | 1999-03-04 | 2002-03-27 | 美国家用产品公司 | N-substituted indolines as estrogenic agents |
| CN101652346A (en) * | 2007-02-01 | 2010-02-17 | 约瑟夫·傅立叶大学 | Novel indole derivatives, process for their preparation and use, especially as antibacterial agents |
| WO2010051374A1 (en) * | 2008-10-31 | 2010-05-06 | Pain Therapeutics, Inc. | Analgesic that binds filamin a |
Non-Patent Citations (1)
| Title |
|---|
| 1-Ketolilolidine and Some of Its Reactions;Henry Rapoport，等;《Journal of Organic Chemistry》;19580201;第23卷(第2期);第248-251页 * |
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| CN103664733A (en) | 2014-03-26 |
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