GB766036A - New 5-benzyloxy-indole derivatives and process for the production thereof - Google Patents
New 5-benzyloxy-indole derivatives and process for the production thereofInfo
- Publication number
- GB766036A GB766036A GB960055A GB960055A GB766036A GB 766036 A GB766036 A GB 766036A GB 960055 A GB960055 A GB 960055A GB 960055 A GB960055 A GB 960055A GB 766036 A GB766036 A GB 766036A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- acid
- free acid
- alkanol
- benzyloxy
- 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.)
- Expired
Links
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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention comprises indole derivatives of the formula <FORM:0766036/IV(b)/1> where X is a hydrogen atom or an alkyl group containing up to 5 carbon atoms, and their preparation by heating in boiling anhydrous dioxan, benzene or its methyl homologues, or, when X is an alkyl group, an alkanol containing up to 5 carbon atoms, a -keto adipic acid p-benzyloxy-phenyl-hydrazone or a dialkyl ester thereof in the presence of a mineral acid. When the free acid is heated in an alkanol the process is a combined esterification and cyclization. Alkaline hydrolysis of the esters of the invention gives the parent acid. The phenyl hydrazone starting material is prepared by coupling diazotized p-benzyloxyaniline with a -carbethoxycyclopentanone and hydrolysing the coupling product in an alkaline medium followed, when the ester is required, by esterification with an aliphatic diazo compound or an alkanol containing up to 5 carbon atoms. Examples described the preparation of the free acid of the invention and its diethyl, dimethyl and di-2-methylbutyl esters, and the hydrolysis of the latter two compounds to the free acid again.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB960055A GB766036A (en) | 1955-04-01 | 1955-04-01 | New 5-benzyloxy-indole derivatives and process for the production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB960055A GB766036A (en) | 1955-04-01 | 1955-04-01 | New 5-benzyloxy-indole derivatives and process for the production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB766036A true GB766036A (en) | 1957-01-16 |
Family
ID=9875115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB960055A Expired GB766036A (en) | 1955-04-01 | 1955-04-01 | New 5-benzyloxy-indole derivatives and process for the production thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB766036A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2947757A (en) * | 1956-02-21 | 1960-08-02 | Francesco Vismara Societa Per | Process for preparing 5-hydroxy-tryptamine through new intermediates |
-
1955
- 1955-04-01 GB GB960055A patent/GB766036A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2947757A (en) * | 1956-02-21 | 1960-08-02 | Francesco Vismara Societa Per | Process for preparing 5-hydroxy-tryptamine through new intermediates |
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