CH156442A - Process for the preparation of a derivative of 3-nitro-4-oxybenzamide. - Google Patents

Process for the preparation of a derivative of 3-nitro-4-oxybenzamide.

Info

Publication number
CH156442A
CH156442A CH156442DA CH156442A CH 156442 A CH156442 A CH 156442A CH 156442D A CH156442D A CH 156442DA CH 156442 A CH156442 A CH 156442A
Authority
CH
Switzerland
Prior art keywords
nitro
preparation
oxybenzamide
derivative
phenylenediamine
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 CH156442A publication Critical patent/CH156442A/en

Links

Description

  

  Verfahren zur Darstellung eines     Abkömmlings    des     3-Nitro-4-oaybenzamids.       Es wurde gefunden, dass man zu neuen  wertvollen Zwischenprodukten gelangt, wenn  man     3-Nitro-4-acyloxybenzoesäurehalogenide     
EMI0001.0004     
         (Ac=Acidyl,    z.

   B.     0HsC0-,        H5C#",OOC-;          Hlg    - Halogen)     bezw.    ihre     Kernsubstitutions-          produkte    mit solchen aromatischen     Amino-          verbindungen    umsetzt, welche in     ortho-Stellung     zur     Aminogruppe    eine     Amino-,        Hydroxyl-          oder        Mercaptogruppe,

      oder in     peri-Stellung     zur     Aminogruppe    eine weitere     Aminogruppe     enthalten, und die Umsetzungsprodukte, so  weit sie noch keine     heterocyklischen    Verbin  dungen darstellen, mit zum     Ringschluss    füh  renden Mitteln behandelt.    Gegenstand vorliegender Erfindung ist  nun ein Verfahren zur Darstellung eines Ab  kömmlings des     3-Nitro-4-oxybenzamids,    da  durch gekennzeichnet, dass man     3-Nitro-4-          acyl-oxyberizoesäurebalogenid    mit     1.2-Pheny-          lendiamin    umsetzt.  



  Die so erhaltene Substanz ist ein wert  volles Zwischenprodukt zur Herstellung von  Farbstoffen.  



  <I>Beispiel:</I>  <B>10,8</B>     gr        1.2-Phenylendiamin    werden in  700 cm' Wasser gelöst, 70     gr    kristallisiertes       Natriumacetat    zugesetzt und unter heftigem  Rühren bei<B>600</B> 24,3     gr        3-Nitro-4-acetoxy-          benzoylchlorid    rasch eingetragen. Die Reak  tion tritt sofort ein und das Umsetzungspro  dukt scheidet sich aus.

   Aus     Äthylo,lkobol     umkristallisiert, bildet es gelblich gefärbte       Nädelchen    vom Schmelzpunkt<B>186'.</B> Es ist  in verdünnter Natronlauge mit tiefgelber  Farbe löslich, reagiert nicht mehr mit sal-           petriger    Säure und besitzt demnach die  Formel  
EMI0002.0002     




  Process for the preparation of a derivative of 3-nitro-4-oaybenzamide. It has been found that new valuable intermediates are obtained if 3-nitro-4-acyloxybenzoic acid halides are used
EMI0001.0004
         (Ac = acidyl, e.g.

   B. 0HsC0-, H5C # ", OOC-; Hlg - halogen) or their core substitution products with those aromatic amino compounds which have an amino, hydroxyl or mercapto group in the ortho position to the amino group,

      or contain a further amino group in the peri-position to the amino group, and the reaction products, insofar as they do not yet represent heterocyclic compounds, are treated with agents leading to ring closure. The present invention now provides a method for the preparation of a derivative of 3-nitro-4-oxybenzamide, characterized in that 3-nitro-4-acyl-oxyberizoic acid halide is reacted with 1,2-phenylenediamine.



  The substance obtained in this way is a valuable intermediate for the production of dyes.



  <I> Example: </I> <B> 10.8 </B> g 1,2-phenylenediamine are dissolved in 700 cm 'of water, 70 g crystallized sodium acetate are added and with vigorous stirring at <B> 600 </B> 24 , 3 grams of 3-nitro-4-acetoxybenzoyl chloride entered quickly. The reaction occurs immediately and the conversion product is eliminated.

   Recrystallized from ethyl alcohol, it forms yellowish needles with a melting point of <B> 186 '. </B> It is soluble in dilute caustic soda with a deep yellow color, no longer reacts with hydrochloric acid and thus has the formula
EMI0002.0002


 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Abkömm lings des 3-Nitro-4-oxybenzamids, dadurch gekennzeichnet, dass man ein 3-Nitro-4-acyl- oxybenzoesäurehalogenid mit 1.2-Phenylen- diamin umsetzt. Das neue Produkt bildet aus Methylal kohol umkristallisiert gelbliche Nädelchen vom Schmelzpunkt 186 . Es ist in verdünnter Natronlauge mit tiefgelber Farbe löslich, und reagiert nicht mehr mit salpetriger Säure. PATENT CLAIM: Process for the preparation of a descendant of 3-nitro-4-oxybenzamide, characterized in that a 3-nitro-4-acyl oxybenzoic acid halide is reacted with 1,2-phenylenediamine. The new product forms yellowish needles with a melting point of 186 when recrystallized from methyl alcohol. It is soluble in dilute caustic soda with a deep yellow color and no longer reacts with nitrous acid.
CH156442D 1930-06-27 1931-06-13 Process for the preparation of a derivative of 3-nitro-4-oxybenzamide. CH156442A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE156442X 1930-06-27

Publications (1)

Publication Number Publication Date
CH156442A true CH156442A (en) 1932-08-15

Family

ID=5677817

Family Applications (1)

Application Number Title Priority Date Filing Date
CH156442D CH156442A (en) 1930-06-27 1931-06-13 Process for the preparation of a derivative of 3-nitro-4-oxybenzamide.

Country Status (1)

Country Link
CH (1) CH156442A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5375713A (en) * 1993-12-08 1994-12-27 Philips Electronics North America Corporation Packed electric lamp of triangular planform

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5375713A (en) * 1993-12-08 1994-12-27 Philips Electronics North America Corporation Packed electric lamp of triangular planform

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