CH127128A - Process for the preparation of N-methyldianisylisatin. - Google Patents

Process for the preparation of N-methyldianisylisatin.

Info

Publication number
CH127128A
CH127128A CH127128DA CH127128A CH 127128 A CH127128 A CH 127128A CH 127128D A CH127128D A CH 127128DA CH 127128 A CH127128 A CH 127128A
Authority
CH
Switzerland
Prior art keywords
methyldianisylisatin
preparation
dianisylisatin
alcohol
melting point
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH127128A publication Critical patent/CH127128A/en

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 N-Methyldianisylisatin.    Bis jetzt wurde allgemein     angenommen,     dass die Wirkung plenolartiger Abführmittel  mit dem Vorhandensein einer oder mehrerer  freier oder nur schwach blockierter Hydroxyl  gruppen zusammenhängt (Kaufmann,  Bei  trag zur Theorie der Laxantia. , Pharmazeu  tische Zeitung, Nr. 77, 1926, Seite 1202).  



  Es hat sich nun überraschenderweise er  geben, dass die Allyl- und Aralkylderivate  der Diphenolisatine, welche keine freie Hy  droxylgruppe mehr besitzen und auch nicht  verseifbar sind, ausgezeichnete Abführmittel  darstellen, die schon in sehr geringen Dosen  eine gleichmässie g und sichere Wirkung ent  falten.  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung des     N-Methyl-          dianisylisatins,    welches dadurch gekennzeich  net ist, dass man auf Dianisylisatin, dem die  Konstitutionsformel  
EMI0001.0004     
    zukommt, ein Methylierungsmittel in der  Wärme einwirken lässt.  



  Das N-Methyldianisylisatin bildet     Kxi-          stalle    vom Schmelzpunkt 153  . Es stellt eine  neutral reagierende, sehr beständige Verbin  dung dar, welche mit Ferricyankalium und  Natronlauge keine Farbreaktion mehr gibt.  In Wasser, Alkalien und Säuren ist es unlös  lich; in den üblichen organischen Lösungs  mitteln, Alkohol, Benzol, Eisessig, löst es  sich in der Wärme leicht. Das     N-Metlyl-          dianisylisatin    soll als Arzneimittel verwendet  werden.  



  Beispiel:  10 Teile Dianisylisatin worden mit einer  Lösung von 1.6 Teilen Ätznatron in 30 Teilen  Wasser unter Zugabe von 3,7 feilen     Di-          methylsulfat    1 Stunde amu Rückflusskühler  gekocht. Hernach wird abgekühlt, filtriert  und aus Alkohol umkristallisiert. Man ge  winnt das     N-Methyldianisylisatin    als Kri  stallpulver vom Schmelzpunkt 153  .



  Process for the preparation of N-methyldianisylisatin. Until now, it was generally assumed that the effect of plenol-like laxatives is related to the presence of one or more free or only weakly blocked hydroxyl groups (Kaufmann, Contribution to the theory of Laxantia., Pharmazeu tables newspaper, No. 77, 1926, page 1202).



  It has now surprisingly been found that the allyl and aralkyl derivatives of diphenolisatins, which no longer have a free hydroxyl group and are also not saponifiable, are excellent laxatives which even in very small doses develop a uniform and safe effect. The subject matter of the present patent is a process for the preparation of N-methyl dianisylisatin, which is characterized in that one uses dianisylisatin, which has the constitutional formula
EMI0001.0004
    comes, a methylating agent can act in the heat.



  The N-methyldianisylisatin forms crystals with a melting point of 153. It is a neutrally reacting, very stable compound, which no longer reacts with ferricyanide and sodium hydroxide solution. It is insoluble in water, alkalis and acids; in the usual organic solvents, alcohol, benzene, glacial acetic acid, it dissolves easily when heated. The N-methyldianisylisatin should be used as a drug.



  Example: 10 parts of dianisylisatin are boiled in a reflux condenser for 1 hour with a solution of 1.6 parts of caustic soda in 30 parts of water with the addition of 3.7 parts of dimethyl sulfate. It is then cooled, filtered and recrystallized from alcohol. The N-methyldianisylisatin is obtained as crystal powder with a melting point of 153.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung voii N-Metliyl- dianisylisatzn, dadurch gekennzeichnet, dass man auf Dianisylisatin, welchem die Konsti tutionsformel EMI0002.0001 zukommt, ein Methylierungsmittel in der Wärme einwirken lässt. Das N-Methyldianisylisatin bildet Kri stalle vom Schmelzpunkt 153 . Es stellt eine neutral reagierende, sehr beständige Verbin dung dar, welche mit Ferricyankalium und Natronlauge keine Farbreaktion mehr gibt. In Wasser, Alkalien und Säuren ist es un löslich; in den üblichen organischen Lösungs mitteln, Alkohol, Benzol, Eisessig, löst es sich in der Wärme leicht. PATENT CLAIM: Process for the preparation of N-Metliyl- dianisylisatzn, characterized in that one on dianisylisatin, which the constitution formula EMI0002.0001 comes, a methylating agent can act in the heat. The N-methyldianisylisatin forms crystals with a melting point of 153. It is a neutrally reacting, very stable compound, which no longer reacts with ferricyanide and sodium hydroxide solution. It is insoluble in water, alkalis and acids; in the usual organic solvents, alcohol, benzene, glacial acetic acid, it dissolves easily when heated. Das N-Metlyldianisyli- satin soll als Arzneimittel verwendet werden. The N-Metlyldianisyli- satin should be used as a drug.
CH127128D 1926-10-09 1926-10-09 Process for the preparation of N-methyldianisylisatin. CH127128A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH127128T 1926-10-09

Publications (1)

Publication Number Publication Date
CH127128A true CH127128A (en) 1928-08-16

Family

ID=4385679

Family Applications (1)

Application Number Title Priority Date Filing Date
CH127128D CH127128A (en) 1926-10-09 1926-10-09 Process for the preparation of N-methyldianisylisatin.

Country Status (1)

Country Link
CH (1) CH127128A (en)

Similar Documents

Publication Publication Date Title
CH127128A (en) Process for the preparation of N-methyldianisylisatin.
CH125398A (en) Process for the preparation of N-methyldianisylisatin.
CH125397A (en) Process for the preparation of di-O-isopropylphenolisatin.
AT113002B (en) Process for the preparation of monoboric acid choline.
CH124026A (en) Process for the preparation of dianisylisatin.
CH125395A (en) Process for the preparation of diphenetylisatin.
DE963514C (en) Process for the production of poorly soluble, crystallized streptomycin and dihydrostreptomycin salts
DE464527C (en) Process for the preparation of alkyl and aralkyl derivatives of diphenolisatins
AT112135B (en) Process for the preparation of basic oxime ethers and their salts.
AT226217B (en) Process for the preparation of the new 5-chloro-4-nitro-2-aminophenol
DE495336C (en) Process for the preparation of basic oxime ethers and their salts
AT153205B (en) Process for the preparation of 3,5-diiodo-4-oxyacetophenone.
DE540534C (en) Process for the preparation of alkoxy derivatives of 2-oxynaphthalene-3-carboxylic acid
AT99681B (en) Process for the preparation of easily soluble salts of quinine.
AT95240B (en) Process for the preparation of 1-arylamido-2-naphthols.
AT136396B (en) Process for the preparation of 1-phenyl-2,3-dimethyl-4-alkylpyrazolonen- (5).
AT55403B (en) Process for the production of quinine esters of aromatic amino acids.
DE339101C (en) Process for the preparation of ethers of p-oxyphenylcarbamide
AT48354B (en) Process for the preparation of amino derivatives of oxyarylarsinic acids and their reduction products.
CH199680A (en) Process for the preparation of 2,4-dioxo-3,3-di-n-propyl-5-bromo-6-methyl-tetrahydropyridine.
CH125396A (en) Process for the preparation of di-O-benzylguaiacolisatin.
CH134220A (en) Process for the production of choline monoborate from choline and boric acid.
CH199679A (en) Process for the preparation of 2,4-dioxo-3,3-di-n-propyl-5-chloro-tetrahydropyridine.
CH193773A (en) Process for the preparation of 2,4-dioxo-3,3-diethyl-5-chloro-tetrahydropyridine.
CH232491A (en) Process for the production of an estrogenic substance.