CH145032A - Process for the preparation of 6-chloro-7-methylisatin. - Google Patents

Process for the preparation of 6-chloro-7-methylisatin.

Info

Publication number
CH145032A
CH145032A CH145032DA CH145032A CH 145032 A CH145032 A CH 145032A CH 145032D A CH145032D A CH 145032DA CH 145032 A CH145032 A CH 145032A
Authority
CH
Switzerland
Prior art keywords
chloro
methylisatin
preparation
heated
reaction
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH145032A publication Critical patent/CH145032A/en

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Description

  

  Verfahren zur Darstellung von     6-Chlor-7-methylisatino       Gegenstand dieses Patentes ist ein  Verfahren zur Darstellung von     6-Chlor-7-          methylisatin,    welches dadurch gekennzeich  net ist, dass man     Cyanform.-(2-methyl-8-          chlor-anilid)    mit einem sauren Kondensa  tionsmittel erhitzt und das so gebildete ss  Isatinimid mit verseifenden Mitteln behan  delt.  



  <I>Beispiel:</I>  Man schmilzt 80 Gewichtsteile Alumi  niumchlorid und 20 Gewichtsteile Natrium  chlorid zusammen und trägt     allmählich    bei  100 bis 105   C 19 Gewichtsteile     Cyanform-          (2-methyl-8-chloranilid)    vom Schmelzpunkt  106 bis<B>108'</B> C (schmilzt unter Aufschäumen)  unter Rühren ein. Die Temperatur steigt da  bei bis auf 120   C. Nach fünf Minuten etwa  ist die     Isatinimidbildung    beendet. Man gibt  die Schmelze auf Eis,     erwärmt    die ange  säuerte Flüssigkeit kurz, saugt das in orange  gefärbten Flocken ausgeschiedene     Isatin    ab,  wäscht es mit Wasser und trocknet es.

      Man erhält praktisch reines     6-Chlor-7-me-          thylisatin.    Nach dem     Umkristallisieren    aus  Eisessig schmilzt dieses bekannte     Isatin    bei  245 bis 246   C. Man kann auch das Ver  fahren so ausführen, dass man zu     dem'Alu-          miniumchlorid    an Stelle von N     atriumchlorid          Trichlorbenzol    oder dergleichen als Verdün  nungsmittel zusetzt.



  Process for the preparation of 6-chloro-7-methylisatino The subject of this patent is a process for the preparation of 6-chloro-7-methylisatin, which is characterized in that cyanoform .- (2-methyl-8-chloro-anilide) heated with an acidic condensation agent and the ss isatinimide thus formed is treated with saponifying agents.



  <I> Example: </I> 80 parts by weight of aluminum chloride and 20 parts by weight of sodium chloride are melted together and 19 parts by weight of cyanoform (2-methyl-8-chloroanilide) with a melting point of 106 to 108 are gradually added at 100 to 105 C '</B> C (melts while foaming) while stirring. The temperature rises up to 120 C. After about five minutes, isatinimide formation is complete. The melt is poured onto ice, the acidified liquid is briefly heated, the isatin, which has separated out in orange flakes, is filtered off with suction, washed with water and dried.

      Practically pure 6-chloro-7-methylisatin is obtained. After recrystallization from glacial acetic acid, this known isatin melts at 245 to 246 ° C. The process can also be carried out in such a way that trichlorobenzene or the like is added as a diluent to the aluminum chloride instead of n atrium chloride.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von b-Chlor- 7-methylisatin, dadurch gekennzeichnet, dass man Cyanform-(2-methyl-3-chlor-anilid) mit einem sauren Kondensationsmittel erhitzt und das so gebildete ss-Iäatinimid mit ver- seifenden Mitteln behandelt. U NTERANSPRüCHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man das Reaktions gemisch auf<B>100</B> bis 120 C erhitzt. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Reaktion in einer Natrium-Aluminiuinchloridschmelze ausführt. 3. PATENT CLAIM: Process for the preparation of b-chloro-7-methylisatin, characterized in that cyanoform (2-methyl-3-chloro-anilide) is heated with an acidic condensing agent and the so-formed ß-Iäatinimide is treated with saponifying agents . SUB-CLAIMS 1. Process according to patent claim, characterized in that the reaction mixture is heated to between 100 and 120 ° C. 2. The method according to claim, characterized in that the reaction is carried out in a sodium-aluminum chloride melt. 3. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eines organischen Verdün nungsmittels vornimmt. Process according to patent claim, characterized in that the reaction is carried out in the presence of an organic diluent.
CH145032D 1928-03-29 1929-03-27 Process for the preparation of 6-chloro-7-methylisatin. CH145032A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE145032X 1928-03-29
CH141875T 1929-03-27

Publications (1)

Publication Number Publication Date
CH145032A true CH145032A (en) 1931-01-31

Family

ID=25713937

Family Applications (1)

Application Number Title Priority Date Filing Date
CH145032D CH145032A (en) 1928-03-29 1929-03-27 Process for the preparation of 6-chloro-7-methylisatin.

Country Status (1)

Country Link
CH (1) CH145032A (en)

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