CH194648A - Process for the preparation of a 4,5-alkyl-substituted 2-aminodiaryl ketone. - Google Patents

Process for the preparation of a 4,5-alkyl-substituted 2-aminodiaryl ketone.

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Publication number
CH194648A
CH194648A CH194648DA CH194648A CH 194648 A CH194648 A CH 194648A CH 194648D A CH194648D A CH 194648DA CH 194648 A CH194648 A CH 194648A
Authority
CH
Switzerland
Prior art keywords
ketone
aminodiaryl
substituted
alkyl
preparation
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 CH194648A publication Critical patent/CH194648A/en

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Description

  

  Verfahren zur Darstellung eines     4,5-alkylsubstituierten        2-Aminodiarylketons.       Gegenstand des vorliegenden Zusatzpaten  tes ist ein Verfahren zur Darstellung eines       4,5-alkylsubstituierten        2-Aminodiarylketons,     welches dadurch gekennzeichnet ist, dass  man     o-Chlorbenzoylchlorid    in Gegenwart von  Aluminiumchlorid auf     1.-Acetamino    - 3,4 -     di-          methylbenzol        einwirken    lässt     (Friedel-Crafts-          sche    Reaktion)

   und in dem so erhaltenen       Keton    die     Acetaminogruppe    zur     Amino-          gruppe    verseift.  



  <I>Beispiel:</I>  30     Gewichsteile        Acetamino-3,4-dimethyl-          benzol    werden in 250 Raumteilen Schwefel  kohlenstoff mit 50 Gewichtsteilen     o-Chlor-          benzoylchlorid    verrührt und alsdann unter  Kühlung mit Eiswasser mit 200 Gewichts  teilen gepulvertem Aluminiumchlorid in Por  tionen versetzt. Die Reaktionsmasse wird  eine Stunde bei gewöhnlicher Temperatur  verrührt und sodann bis zum Nachlassen der       Salzsäureentwicklung    auf dem Wasserbade  gelinde erwärmt.

   Der     Schwefelkohlenstoff       wird entweder nach längerem Stehen ab  gegossen oder sofort     abdestilliert        und    die  Reaktionsmasse mit Eis und Salzsäure zer  setzt. Man saugt ab, wäscht mit Salzsäure  bis zur Beseitigung der Aluminiumsalze nach  und alsdann mit     verdünnter    Natronlauge zur  Entfernung überschüssiger     o-Chlorbenzoe-          säure.    Nach dem     Neutralwaschen        wird    das  so     gewonnene        2-Acetamino-4,5-dimethyl-2'-          chlorbenzophenon    aus Methanol kristallisiert,  wobei es in derben,

   farblosen Prismen vom  Schmelzpunkt 173   C anfällt, die sich in       konzentrierter    Schwefelsäure mit gelber  Farbe lösen.  



  Wird diese     Acetylaminoverbindung    mit  Salzsäure durch Kochen verseift und die       Reaktionsmasse    in überschüssige     kalte    ver  dünnte Natronlauge eingerührt, so wird das  2     -Amino    - 4,5 -     dimethyl    - 2'-     chlorbenzophenon     in gelben Prismen vom     Schmelzpunkt    120' C  erhalten. Das     2-Amino-4,5-dimethyl-2'-chlor-          benzophenon    ist eine neue Verbindung und      soll als Zwischenprodukt für Farbstoffe Ver  wendung finden.



  Process for the preparation of a 4,5-alkyl-substituted 2-aminodiaryl ketone. The subject of the present additional patent is a process for the preparation of a 4,5-alkyl-substituted 2-aminodiaryl ketone, which is characterized in that o-chlorobenzoyl chloride is allowed to act on 1.-acetamino-3,4-dimethylbenzene in the presence of aluminum chloride ( Friedel-Crafts reaction)

   and in the ketone obtained in this way, the acetamino group is saponified to form the amino group.



  <I> Example: </I> 30 parts by weight of acetamino-3,4-dimethylbenzene are mixed in 250 parts by volume of carbon disulfide with 50 parts by weight of o-chlorobenzoyl chloride and then, while cooling with ice water, with 200 parts by weight of powdered aluminum chloride in portions offset. The reaction mass is stirred for one hour at normal temperature and then gently warmed on the water bath until the evolution of hydrochloric acid subsides.

   The carbon disulfide is either poured off after prolonged standing or distilled off immediately and the reaction mass is set with ice and hydrochloric acid. It is filtered off with suction, washed with hydrochloric acid until the aluminum salts are eliminated and then with dilute sodium hydroxide solution to remove excess o-chlorobenzoic acid. After washing neutral, the 2-acetamino-4,5-dimethyl-2'-chlorobenzophenone obtained in this way is crystallized from methanol, whereby it is

   colorless prisms with a melting point of 173 C are obtained, which dissolve in concentrated sulfuric acid with a yellow color.



  If this acetylamino compound is saponified with hydrochloric acid by boiling and the reaction mixture is stirred into excess cold dilute sodium hydroxide solution, the 2-amino-4,5-dimethyl-2'-chlorobenzophenone is obtained in yellow prisms with a melting point of 120 ° C. 2-Amino-4,5-dimethyl-2'-chlorobenzophenone is a new compound and should be used as an intermediate for dyes.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines 4,5-al- kylsubstituierten 2-Aminodiarylketons, da durch gekennzeichnet, dass man o-Chlorben- zoylchlorid in Gegenwart von Aluminium chlorid auf 1-Acetamino-3,4,dimethylbenzol einwirken lässt und in dem so erhaltenen Keton die Acetaminogruppe zur Amino- gruppe verseift. PATENT CLAIM: Process for the preparation of a 4,5-alkyl-substituted 2-aminodiaryl ketone, characterized in that o-chlorobenzoyl chloride is allowed to act on 1-acetamino-3,4-dimethylbenzene in the presence of aluminum chloride and in the resultant Ketone saponifies the acetamino group to the amino group. Das so erhaltene 2-Amino-4,5-dimethyl- 2'-chlorbenzoplienon bildet gelbe Prismen vom Schmelzpunkt<B>EN'</B> C. The 2-amino-4,5-dimethyl-2'-chlorobenzoplienone thus obtained forms yellow prisms with a melting point of <B> EN '</B> C.
CH194648D 1934-11-20 1935-11-18 Process for the preparation of a 4,5-alkyl-substituted 2-aminodiaryl ketone. CH194648A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE194648X 1934-11-20
CH189404T 1935-11-18

Publications (1)

Publication Number Publication Date
CH194648A true CH194648A (en) 1937-12-15

Family

ID=25721781

Family Applications (1)

Application Number Title Priority Date Filing Date
CH194648D CH194648A (en) 1934-11-20 1935-11-18 Process for the preparation of a 4,5-alkyl-substituted 2-aminodiaryl ketone.

Country Status (1)

Country Link
CH (1) CH194648A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0211588A1 (en) * 1985-07-29 1987-02-25 Ortho Pharmaceutical Corporation Process for preparing 2-acyl-3,4-dialkoxyanilines
EP0212868A1 (en) * 1985-07-29 1987-03-04 Ortho Pharmaceutical Corporation Process for preparing 2-acyl-3,4-dialkoxyanilines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0211588A1 (en) * 1985-07-29 1987-02-25 Ortho Pharmaceutical Corporation Process for preparing 2-acyl-3,4-dialkoxyanilines
EP0212868A1 (en) * 1985-07-29 1987-03-04 Ortho Pharmaceutical Corporation Process for preparing 2-acyl-3,4-dialkoxyanilines

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