DE451957C - Process for the preparation of oxindole-3-propionic acid - Google Patents

Process for the preparation of oxindole-3-propionic acid

Info

Publication number
DE451957C
DE451957C DEC37829D DEC0037829D DE451957C DE 451957 C DE451957 C DE 451957C DE C37829 D DEC37829 D DE C37829D DE C0037829 D DEC0037829 D DE C0037829D DE 451957 C DE451957 C DE 451957C
Authority
DE
Germany
Prior art keywords
oxindole
propionic acid
acid
preparation
isatin
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
DEC37829D
Other languages
German (de)
Inventor
Dr Kurt Schmidt
Dr Walter Schoeller
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 VORM E SCHERING
Original Assignee
CHEM FAB VORM E SCHERING
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 VORM E SCHERING filed Critical CHEM FAB VORM E SCHERING
Priority to DEC37829D priority Critical patent/DE451957C/en
Application granted granted Critical
Publication of DE451957C publication Critical patent/DE451957C/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Darstellung von Oxindol-3-propionsäure. Nach dem Verfahren des Hauptpatents wird Oxindol-3-essigsäure in der Weise dargestellt, daß man Isatin mit Malonsäure, zweckmäßig in molekularen Mengen, zusammenschmilzt und die so erhaltene Oxindol-3-methincarbonsäure mit Reduktionsmitteln behandelt. Ersetzt man gemäß vorliegender Erfindung das Isatin durch Oxindolaldehyd und verfährt in analoger Weise, so gelangt man über die zunächst gebildete Oxindol-3-acrylsäure zur Oxindol-3-propionsäure.Process for the preparation of oxindole-3-propionic acid. After the procedure of the main patent, oxindole-3-acetic acid is represented in such a way that isatin with malonic acid, expediently in molecular amounts, melts together and the resulting Oxindole-3-methinecarboxylic acid treated with reducing agents. Replaced according to the present Invention the isatin by oxindolaldehyde and proceeds in an analogous manner, so arrives one via the initially formed oxindole-3-acrylic acid to oxindole-3-propionic acid.

Beispiel. Molekulare Mengen Oxindalaldehyd und Malonsäure werden, fein verrieben, im Metallbad bei i so bis 16o° C so lange verschmolzen, bis die Entwicklung von Kohlensäure und Wasserdampf aufgehört hat. Nach dem Erkalten wird die rotbraune Schmelze in Normalnatronlauge gelöst, die rotbraune Lösung mit verdünnter Salzsäure angesäuert und die ausgefallene Oxindol-3-acrylsäure abgesaugt. Durch mehrmaliges Umkristallisieren aus verdünntem, heißem Alkohol und längeres Kochen mit Tierkohle erhält man eine gelbrote, in kleinen Nadelbüscheln kristallisierende Verbindung, die sich bei 2I2° C zersetzt, sich in Alkohol und Eisessig ziemlich leicht, in Äther und Essigester schwerer und in heißem Wasser nur sehr schwer löst. In Alkalien ist sie ziemlich leicht löslich; ihre sodaalkalische Lösung entfärbt Kaliumpermanganat fast augenblicklich.Example. Molecular amounts of oxindalaldehyde and malonic acid are finely rubbed, fused in a metal bath at 1 to 16o ° C until the The development of carbonic acid and water vapor has ceased. After it has cooled down the red-brown melt dissolved in normal sodium hydroxide solution, the red-brown solution with dilute Acidified hydrochloric acid and sucked off the precipitated oxindole-3-acrylic acid. By repeated recrystallization from dilute, hot alcohol and prolonged boiling with animal charcoal you get a yellow-red color that crystallizes in small tufts of needles Compound that decomposes at 2I2 ° C pretty much dissolves in alcohol and glacial acetic acid Easily dissolves, more difficult in ether and ethyl acetate and very difficult to dissolve in hot water. It is fairly easily soluble in alkalis; their soda-alkaline solution is discolored Potassium permanganate almost instantly.

Im Gegensatz hierzu führt die Perkinsche Zimmtsäuresynthese in ihrer Anwendung auf den Oxindolaldehyd nicht zu der erwarteten Acrvlsäure, sondern zu einer indifferenten Verbindung (vgl. Chemisches Zentralblatt 1924, Bd.1, S.328).In contrast to this, Perkin's synthesis of room acid leads to their Application to the oxindole aldehyde not to the expected acrylic acid, but to an indifferent compound (see Chemisches Zentralblatt 1924, Bd.1, p.328).

Die Oxindol-3-acrylsäure wird in der berechneten Menge Normalnatronlauge gelöst und durch überschüssiges Aluminiumamalgan reduziert. Die Aufarbeitung des Rohproduktes erfolgt wie im Hauptpatent angegeben. Die erhaltene Oxindol-3-propionsäure bildet, aus heißem Wasser umkristallisiert, schwach gelblich gefärbte Prismen vom Schmelzpunkt 2o8°. Sie ist leicht löslich in Alkohol, Äther und Eisessig, schwerer in Petroläther und heißem Wasser, fast unlöslich in kaltem Wasser.The oxindole-3-acrylic acid is normal sodium hydroxide solution in the calculated amount dissolved and reduced by excess aluminum amalgan. The processing of the Raw product takes place as indicated in the main patent. The obtained oxindole-3-propionic acid forms, recrystallized from hot water, slightly yellowish colored prisms of the Melting point 208 °. It is easily soluble in alcohol, ether and glacial acetic acid, more difficult in petroleum ether and hot water, almost insoluble in cold water.

Claims (1)

PATENTANSPRUCH: Weitere Ausbildung des durch Patent 431 510 geschützten Verfahrens, dadurch gekennzeichnet, daß man zwecks Darstellung von Oxindol-3-propionsäure an Stelle von Isatin hier Oxindolaldehyd mit Malonsäure, zweckmäßig in molekularen Mengen, zusammenschmilzt und das erhaltene Reaktionsprodukt mit Reduktionsmitteln behandelt.PATENT CLAIM: Further development of the process protected by patent 431 510 , characterized in that, in order to prepare oxindole-3-propionic acid, instead of isatin, oxindole aldehyde is melted together with malonic acid, expediently in molecular amounts, and the reaction product obtained is treated with reducing agents.
DEC37829D 1926-02-12 1926-02-12 Process for the preparation of oxindole-3-propionic acid Expired DE451957C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC37829D DE451957C (en) 1926-02-12 1926-02-12 Process for the preparation of oxindole-3-propionic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC37829D DE451957C (en) 1926-02-12 1926-02-12 Process for the preparation of oxindole-3-propionic acid

Publications (1)

Publication Number Publication Date
DE451957C true DE451957C (en) 1927-11-01

Family

ID=7023009

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC37829D Expired DE451957C (en) 1926-02-12 1926-02-12 Process for the preparation of oxindole-3-propionic acid

Country Status (1)

Country Link
DE (1) DE451957C (en)

Similar Documents

Publication Publication Date Title
DE451957C (en) Process for the preparation of oxindole-3-propionic acid
DE459361C (en) Process for the preparation of nuclear iodine substitution products of oxine sol-3-propionic acid
DE436518C (en) Process for the preparation of nuclear halogen substitution products of oxindole-3-acetic acid
AT106481B (en) Process for the preparation of multiply iodized isatins.
DE429101C (en) Process for the preparation of di- and tetraiodisatin
DE539178C (en) Process for the preparation of hydrogenated amides of nicotinic acid
DE429100C (en) Process for the preparation of an iodine-substituted oxindole
DE462137C (en) Process for the preparation of primary amino alcohols of the quinoline series
CH253710A (en) Process for the preparation of 5,6,7,8-tetrahydroisoquinoline.
DE724161C (en) Process for the preparation of condensation products of the isoquinoline series
US1587866A (en) Monoiodo-oxindol and process of making same
DE451730C (en) Process for the preparation of 6-alkoxy-8-aminoquinolines
DE537106C (en) Process for the preparation of o, o -diphenylphenolphthalein and o, o-dioxydiphenolphthalein and their acetyl derivatives
DE89979C (en)
DE668628C (en) Process for the preparation of alkyl and aralkyl compounds of 3,4-cyclotetramethylene-1-aryl-5-pyrazolones
DE540534C (en) Process for the preparation of alkoxy derivatives of 2-oxynaphthalene-3-carboxylic acid
AT117475B (en) Process for the preparation of substitution products of ß-iodopyridine.
DE739634C (en) Process for the production of polyiodinated compounds of oxydiphenyl acetic acids
DE657106C (en) Process for the preparation of N-methyl-C, C-allylisopropylbarbituric acid
DE595188C (en) Process for the preparation of 4-aminodiphenylamine derivatives
DE669187C (en) Process for the production of vitamin B.
DE665513C (en) Process for the preparation of 3,5-diiodo-4-oxyacetophenone
DE659496C (en) Process for the preparation of iodine and 2-phenylquinoline-4-carboxylic acids containing free or etherified oxy groups
DE627697C (en) Process for the production of nitrophenols
DE501724C (en) Process for the preparation of derivatives of diphenolisatin and its substitution products