GB266539A - The manufacture of new halogen substituted oxindol-3-acetic acids and homologues thereof - Google Patents

The manufacture of new halogen substituted oxindol-3-acetic acids and homologues thereof

Info

Publication number
GB266539A
GB266539A GB559426A GB559426A GB266539A GB 266539 A GB266539 A GB 266539A GB 559426 A GB559426 A GB 559426A GB 559426 A GB559426 A GB 559426A GB 266539 A GB266539 A GB 266539A
Authority
GB
United Kingdom
Prior art keywords
oxindol
acid
diiodo
monoiodo
halogenated
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
GB559426A
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.)
CHEM FAB AUF ACTIEN
Original Assignee
CHEM FAB AUF ACTIEN
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 CHEM FAB AUF ACTIEN filed Critical CHEM FAB AUF ACTIEN
Priority to GB559426A priority Critical patent/GB266539A/en
Publication of GB266539A publication Critical patent/GB266539A/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
    • C07D209/30—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
    • C07D209/32—Oxygen atoms
    • C07D209/34—Oxygen atoms in position 2

Landscapes

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

Abstract

266,539. Carpmael, W., (Chemische Fabrik auf Actien, vorm. E. Schering). Feb, 27, 1926. Halogenated oxindol-3-acetic acids and their homologues are prepared either by halogenating oxindol-3-acetic acid and its homologues, or by condensing a halogenated isatin or halogenated oxindol-aldehyde with malonic acid and reducing the product. The compounds are useful for the manufacture of pharmaceutical preparations. According to the examples, (1) dichlor-, dibrom-, 5- monoiodo-, and 5 : 7-diiodo-oxindol-3-acetic acids are obtained by treating a solution of oxindol-3- acetic acid with the requisite quantity of chlorine, bromine or iodine chloride; (2) 5-monoiodo-oxindol-3-acetic acid is prepared by heating 5-iodoisatin with malonic acid until carbon dioxide ceases to be evolved, and treating a caustic soda solution of the resulting 5-iodo-oxindol-3-methinecarboxylic acid with aluminium amalgam; 5 : 7- diiodo-oxindol-3-acetic acid is obtained in the same way from 5 : 7-diiodoisatin; (3) 5-monoiodooxindol-3-propionic acid results when 5-monoiodooxindol-aldehvde is heated with malonic acid until carbon dioxide is no longer evolved, and reducing, preferably with aluminium amalgam, the resulting 5-monoiodo-oxindol-3-acrylic acid; (4) by treatment of a solution of oxindol-3-propionic acid with a molecular quantity of iodine chloride, 5- monoiodo-oxindol-3-propionic acid is obtained; (5) 5 : 7-diiodo-oxindol-3-propionic acid is prepared by condensing 5 : 7-diiodo-oxindol-3-aldehyde with malonic acid and then reducing the 5 : 7-diiodo-oxindol-3-acrylic acid obtained. Chloro-, bromo-, and iodo-oxindol-aldehydes are prepared by condensing the corresponding halogen-substituted isatins with 3-oxy-1-thionaphthenecarboxylic acid and treating the resulting halogenated thioindigoid dyestuff with alkali. Oxindol-3-propionic acid is obtained by melting molecular quantities of oxindol-aldehyde and malonic acid together and reducing the product.
GB559426A 1926-02-27 1926-02-27 The manufacture of new halogen substituted oxindol-3-acetic acids and homologues thereof Expired GB266539A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB559426A GB266539A (en) 1926-02-27 1926-02-27 The manufacture of new halogen substituted oxindol-3-acetic acids and homologues thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB559426A GB266539A (en) 1926-02-27 1926-02-27 The manufacture of new halogen substituted oxindol-3-acetic acids and homologues thereof

Publications (1)

Publication Number Publication Date
GB266539A true GB266539A (en) 1927-03-03

Family

ID=9799035

Family Applications (1)

Application Number Title Priority Date Filing Date
GB559426A Expired GB266539A (en) 1926-02-27 1926-02-27 The manufacture of new halogen substituted oxindol-3-acetic acids and homologues thereof

Country Status (1)

Country Link
GB (1) GB266539A (en)

Similar Documents

Publication Publication Date Title
GB266539A (en) The manufacture of new halogen substituted oxindol-3-acetic acids and homologues thereof
GB383154A (en) Manufacture of stabilised halogen derivatives
GB373520A (en) Improvements in the refining of plastic ceramic raw materials
GB308231A (en) Improvements in and relating to the production of substituted benzoyl halides
GB467772A (en) Improvements in and relating to rubber derivatives
GB284035A (en) Improvements in and relating to the production of benzanthrones and their derivatives
GB339436A (en) The manufacture of pyridine compounds
SU77926A1 (en) The method of obtaining 3, 4, 6-trichlorophthalic acid and 3, 4, 6-trichlorophthalic anhydride
GB460249A (en) Manufacture of n-(aminoalkyl)-anthranilic acid alkyl esters
GB183454A (en)
GB489612A (en) Manufacture of fluorene derivatives
GB357743A (en) Improvements in manufacture of polychlornaphthalenes
GB173166A (en) Manufacture of 1-chloro-2-amino-anthraquinone
GB346896A (en) Manufacture of condensation products of the benzanthrone series
GB306390A (en) Improved manufacture of rubber conversion products
GB215021A (en) Manufacture of halogenated oxythionaphthenes
GB300114A (en) Manufacture of indigoid vat dyestuffs
GB349455A (en) Improvements relating to barbituric acid derivatives
GB214864A (en) Manufacture of indigoid dyestuffs and intermediate products
GB198676A (en) Manufacture of highly chlorinated hydro-aromatic products containing nitrogen
GB302147A (en)
GB439807A (en) Manufacture of substituted acid amides
GB357860A (en) Manufacture of organic compounds of antimony
GB229958A (en) Improvements in or relating to the manufacture of esters
GB469633A (en) The manufacture of polycyclic condensation products