CN1102409A - 制备吲哚的方法 - Google Patents
制备吲哚的方法 Download PDFInfo
- Publication number
- CN1102409A CN1102409A CN94106708A CN94106708A CN1102409A CN 1102409 A CN1102409 A CN 1102409A CN 94106708 A CN94106708 A CN 94106708A CN 94106708 A CN94106708 A CN 94106708A CN 1102409 A CN1102409 A CN 1102409A
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- CN
- China
- Prior art keywords
- indoles
- acid
- preparation
- hours
- indoline
- 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.)
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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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明涉及通过相应吲哚-2-羧酸的脱羟基化
制备吲哚的新方法，其特征在于用甲酸处理这些酸。
Description
本发明涉及通过相应的吲哚-2-羧酸的脱羧基化制备吲哚的新方法。
过去通常通过加热吲哚-2-羧酸，使其溶于高度沸腾的叔胺中，在回流下对吲哚-2-羧酸进行脱酸（参见：如Houben-Wey1/Müller，Methoden der Organischen Chemie[有机化学方法];1952，8卷，486页）。
例如，从前于190℃通过加热3-（3-羧基丙基）-5-甲氧基吲哚-2-羧酸（Ⅱ）在N，N-二甲基苯胺或N，N-二乙基苯胺中的溶液24小时制备4-（5-甲氧基-3-吲哚基）丁酸（Ⅰ），即合成roxindol的中间体。
此处的缺点是它需要的高反应温度和与仪器有关的问题，只能在仅少数工厂内生产，长反应时间及因此造成的高能量消耗。
本发明的目的是找到制备吲哚，尤其是Ⅰ的新方法，其中上述缺点被极大地减小或完全不存在。
已发现：如果加热Ⅱ在甲酸中的溶液，得到高产率的Ⅰ。由于一般认为吲哚对酸是高度不稳定的，所以这非常令人惊奇。在试图用其它酸如乙酸，稀硫酸水溶液或稀盐酸水溶液代替甲酸过程中也已说明这一点。或者根本没有反应，或得到低产率Ⅰ并伴随副产品的形成。
可高度成功地将本方法转变成吲哚-2-羧酸。
本发明涉及通过相应吲哚-2-羧酸的脱羧基化制备吲哚的方法，其特征在于用甲酸处理这些酸。
在本方法中，所用甲酸可有利地含有约0-50%的水。反应温度在20到107℃之间，优选在80到107℃之间。在较高温度下要求的反应时间在约1小时到10小时之间，优选在2小时到4小时之间，而在较低温度下要求的反应时间相应较长。
下面给出的百分率为体积百分率。
实施例1
使14.2gⅡ和120g77.4%甲酸的混合物沸腾3小时，然后减压蒸发。把稀氢氧化钠溶液加到残余物中，于40℃简要地用活性碳进行澄清，用盐酸沉淀产品到PH1.5。滤出沉淀Ⅰ，用水洗，于50℃下减压干燥。产量：10.9g。
实施例2
执行实施例1中的方法，只是使用100%的甲酸同时反应时间为2小时。
实施例3
执行实施例1中的方法，只是使用50%甲酸;反应时间：5小时。
实施例4
执行实施例1的方法，只是在80℃;反应时间：30小时。
实施例5
类似于实施例1的方法，从吲哚-2-羧酸得到吲哚。
Claims (1)
- 通过相应吲哚-2-羧酸的脱羧基化制备吲哚的方法，其特征在于用甲酸处理这些酸。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4320835.5 | 1993-06-23 | ||
| DE4320835A DE4320835C1 (de) | 1993-06-23 | 1993-06-23 | Verfahren zur Herstellung von Indolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1102409A true CN1102409A (zh) | 1995-05-10 |
Family
ID=6491009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94106708A Pending CN1102409A (zh) | 1993-06-23 | 1994-06-20 | 制备吲哚的方法 |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0632024A1 (zh) |
| JP (1) | JPH0710837A (zh) |
| KR (1) | KR950000666A (zh) |
| CN (1) | CN1102409A (zh) |
| AU (1) | AU6479794A (zh) |
| CA (1) | CA2126416A1 (zh) |
| CZ (1) | CZ154594A3 (zh) |
| DE (1) | DE4320835C1 (zh) |
| HU (1) | HUT75197A (zh) |
| NO (1) | NO179866C (zh) |
| PL (1) | PL303946A1 (zh) |
| SK (1) | SK75394A3 (zh) |
| TW (1) | TW267162B (zh) |
| ZA (1) | ZA944487B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109694343A (zh) * | 2018-12-19 | 2019-04-30 | 帕潘纳(北京)科技有限公司 | 一种杂环羧酸类化合物的脱羧方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7206261B2 (en) | 2002-08-30 | 2007-04-17 | Ricoh Company, Ltd. | Loading mechanism, drive unit, and information processing apparatus for an information recording medium |
| DE202009015656U1 (de) | 2009-11-26 | 2010-03-18 | Sunpex Technology Co., Ltd. | Antriebsmechanismus eines elektrischen Rollstuhls |
-
1993
- 1993-06-23 DE DE4320835A patent/DE4320835C1/de not_active Expired - Fee Related
-
1994
- 1994-06-15 EP EP94109146A patent/EP0632024A1/de not_active Withdrawn
- 1994-06-17 AU AU64797/94A patent/AU6479794A/en not_active Abandoned
- 1994-06-20 TW TW083105572A patent/TW267162B/zh active
- 1994-06-20 CN CN94106708A patent/CN1102409A/zh active Pending
- 1994-06-20 SK SK753-94A patent/SK75394A3/sk unknown
- 1994-06-21 CA CA002126416A patent/CA2126416A1/en not_active Abandoned
- 1994-06-21 JP JP6138964A patent/JPH0710837A/ja active Pending
- 1994-06-22 HU HU9401887A patent/HUT75197A/hu unknown
- 1994-06-22 KR KR1019940014145A patent/KR950000666A/ko not_active Application Discontinuation
- 1994-06-22 CZ CZ941545A patent/CZ154594A3/cs unknown
- 1994-06-22 NO NO942381A patent/NO179866C/no unknown
- 1994-06-22 ZA ZA944487A patent/ZA944487B/xx unknown
- 1994-06-22 PL PL94303946A patent/PL303946A1/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109694343A (zh) * | 2018-12-19 | 2019-04-30 | 帕潘纳(北京)科技有限公司 | 一种杂环羧酸类化合物的脱羧方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| PL303946A1 (en) | 1995-01-09 |
| NO942381L (no) | 1994-12-27 |
| CA2126416A1 (en) | 1994-12-24 |
| EP0632024A1 (de) | 1995-01-04 |
| CZ154594A3 (en) | 1995-01-18 |
| DE4320835C1 (de) | 1994-09-08 |
| JPH0710837A (ja) | 1995-01-13 |
| HUT75197A (en) | 1997-04-28 |
| SK75394A3 (en) | 1995-03-08 |
| HU9401887D0 (en) | 1994-09-28 |
| AU6479794A (en) | 1995-01-05 |
| KR950000666A (ko) | 1995-01-03 |
| NO942381D0 (zh) | 1994-06-22 |
| ZA944487B (en) | 1995-02-15 |
| NO179866C (no) | 1997-01-02 |
| TW267162B (zh) | 1996-01-01 |
| NO179866B (no) | 1996-09-23 |
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| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |