GB807875A - New indole derivatives - Google Patents

New indole derivatives

Info

Publication number
GB807875A
GB807875A GB440556A GB440556A GB807875A GB 807875 A GB807875 A GB 807875A GB 440556 A GB440556 A GB 440556A GB 440556 A GB440556 A GB 440556A GB 807875 A GB807875 A GB 807875A
Authority
GB
United Kingdom
Prior art keywords
aldehyde
indole
nitrovinyl
nitrovinylindole
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
Application number
GB440556A
Inventor
Edwin Harry Paterson Young
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB440556A priority Critical patent/GB807875A/en
Publication of GB807875A publication Critical patent/GB807875A/en
Expired legal-status Critical Current

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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Abstract

The invention comprises indole derivatives of the formula <FORM:0807875/IV (b)/1> wherein the ring A may optionally be substituted by halogen, alkyl, alkoxy or aralkoxy radicals and wherein R represents hydrogen or an alkyl radical. The compounds are prepared by heating indole-3-aldehydes of the formula <FORM:0807875/IV (b)/2> with a nitroparaffin, preferably in the presence of a basic substance as catalyst. The nitroparaffin reactant is preferably nitromethane, nitroethane, nitropropane or nitro-octane. Suitable catalysts are ammonium acetate, methylamine, n-butylamine and benzylamine. (The Provisional Specification additionally specifies piperidine as a catalyst.) Specified indole-3-aldehyde reactants are indole-3-aldehyde, 5-methoxyindole-3-aldehyde, 6-methoxyindole-3-aldehyde, 5 - benzyloxyindole - 3 - aldehyde, 6 - benzyloxyindole - 3 - aldehyde, 5 - methylindole-3-aldehyde and 5-chloroindole-3-aldehyde. The reaction may be conducted in the presence of a solvent or diluent, such as acetic acid, b -ethoxyethanol or dimethylformamide, or in the presence of an excess of nitroparaffin reactant. The examples describe the preparation of 6-benzyloxy-3-b -nitrovinylindole, 5-benzyloxy - 3 - b - nitrovinylindole, 5 - benzyloxy - 3 - (b - methyl - b - nitrovinyl) - indole, 5 - benzyloxy - 3 - (b - ethyl - b - nitrovinyl) - indole, 5 - benzyloxy - 3 - (b - n - heptyl - b - nitrovinyl)-indole, 5 - methoxy - 3 - (b - methyl - b - nitrovinyl) - indole, 5 - methyl - 3 - b - nitrovinylindole, 5-chloro-3-b -nitrovinylindole, 3-b -nitrovinylindole, 3 - (b - methyl - b - nitrovinyl)-indole and 3-(b -ethyl-b -nitrovinyl)-indole. 5 - Methylindole-3-aldehyde and 5-chloroindole-3-aldehyde are prepared by reacting dimethylformamide with 5-methylindole or 5-chloroindole respectively in presence of phosphorus oxychloride. Specification 807,620 is referred to.
GB440556A 1956-02-13 1956-02-13 New indole derivatives Expired GB807875A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB440556A GB807875A (en) 1956-02-13 1956-02-13 New indole derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB440556A GB807875A (en) 1956-02-13 1956-02-13 New indole derivatives

Publications (1)

Publication Number Publication Date
GB807875A true GB807875A (en) 1959-01-21

Family

ID=9776578

Family Applications (1)

Application Number Title Priority Date Filing Date
GB440556A Expired GB807875A (en) 1956-02-13 1956-02-13 New indole derivatives

Country Status (1)

Country Link
GB (1) GB807875A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3050530A (en) * 1962-08-21 Improved process for the preparation of
CN110746340A (en) * 2019-11-07 2020-02-04 上海易恩化学技术有限公司 Synthetic method of 5-methoxy-2-methyltryptamine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3050530A (en) * 1962-08-21 Improved process for the preparation of
CN110746340A (en) * 2019-11-07 2020-02-04 上海易恩化学技术有限公司 Synthetic method of 5-methoxy-2-methyltryptamine

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