CH115109A - Process for the preparation of 2-aminonaphthalene-1-carboxylic acid. - Google Patents

Process for the preparation of 2-aminonaphthalene-1-carboxylic acid.

Info

Publication number
CH115109A
CH115109A CH115109DA CH115109A CH 115109 A CH115109 A CH 115109A CH 115109D A CH115109D A CH 115109DA CH 115109 A CH115109 A CH 115109A
Authority
CH
Switzerland
Prior art keywords
sep
carboxylic acid
preparation
aminonaphthalene
naphthisatin
Prior art date
Application number
Other languages
German (de)
Inventor
Farbwerke Vorm Meiste Bruening
Original Assignee
Hoechst 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 Hoechst Ag filed Critical Hoechst Ag
Publication of CH115109A publication Critical patent/CH115109A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/47—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung von     2-Aminonaphthalin-l-karbonsäure.       In der deutschen     Patentschrift    Nr. 375616  ist ein Verfahren beschrieben, nach welchem  es gelingt, aus     Isatin    und     seinen    Derivaten  durch     Einwirkung    von Oxydationsmitteln,       wie    zum Beispiel Wasserstoffsuperoxyd, in  Gegenwart von Alkalien,     Anthranilsäure    und  deren Derivate herzustellen.

   So erhält man  zum Beispiel aus     a-Naphthisatin    die     1-Amino-          nal)htlialin-2-karbonsäure        (vergl.    P'.     Fried-          länder    und S.     Littner,    Bericht 48, 1915,  Seite 332, und F. Mayer und     Oppenheimer,     Bericht 51, 1918, Seite 1239). Aus     ss-Naphth-          isatin    ist die     entsprechende        2-Aminonaplitha-          lin-1-karbonsäure    nach diesem Verfahren  aber nicht darzustellen.

     Es wurde nun die Beobachtung gemacht,  dass die Herstellung der     2-Aminonaplithalin-          1-karbonsäure    aus     ss-Naphthisatin    in glatter  Weise zu bewerkstelligen ist, wenn man die       Einwirkung    der Oxydationsmitteln, wie zum  Beispiel Wasserstoffsuperoxyd, in alkalischer       Lösüng    in der Hitze vornimmt.     Unerwar-          teterweise    wird bei dieser einigermassen ge  waltsamen Behandlung die     amidierte    Verbin  dung in keiner Weise angegriffen, und das    war nicht vorher zu sehen.

   Die     2-Amino-          naphthalin-l-karbonsäure    ist ein. wichtiges  Zwischenprodukt zur Herstellung von Farb  stoffen und von pharmazeutischen Produk  ten, und ihre glatte Herstellung bedeutet  einen technischen Fortschritt.-         Beispiel:       6 Teile     ss-Naphthisatin    werden in 45 Tei  len Wasser und 15 Teilen Natronlauge von  40'     B6    heiss gelöst und in die kochende Lö  sung allmählich so viel einer Lösung von  12 Teilen Wasserstoffsuperoxyd 30     %ig    in  dem doppelten Volumen Wasser zugegeben,  bis eine Probe mit verdünnter Salzsäure keine  roten Flocken mehr abscheidet. Bei dieser  Umsetzung ist für ein geräumiges Gefäss und  gutes Umrühren zu sorgen.

   Man filtriert so  dann und macht die Lösung in der gälte mit  Salzsäure kongosauer. Die     2-Aminonaphtlia-          lin-l-karbonsäure    scheidet sich schwach gelb  gefärbt ab und kann durch'     Umlösen    leicht  völlig gereinigt werden. Die Ausbeute be  trägt etwa 90 %.    
EMI0002.0001     
  
    Verwendet <SEP> man <SEP> an <SEP> Stelle <SEP> von <SEP> 12 <SEP> Teilen
<tb>  -\@'asserstoffsuperozy <SEP> d <SEP> eine <SEP> äquivalente <SEP> Menge
<tb>  Persalze, <SEP> z. <SEP> B. <SEP> Natriumsuperoxyd <SEP> oder <SEP> Na  triumperborat, <SEP> so <SEP> erhält <SEP> man <SEP> ein <SEP> bleiches
<tb>  Resultat.



  Process for the preparation of 2-aminonaphthalene-1-carboxylic acid. German Patent No. 375616 describes a process by which it is possible to produce anthranilic acid and its derivatives from isatin and its derivatives by the action of oxidizing agents, such as hydrogen peroxide, in the presence of alkalis.

   For example, 1-amino nal) htlialin-2-carboxylic acid is obtained from α-naphthisatin (see P. Friedlander and S. Littner, Report 48, 1915, page 332, and F. Mayer and Oppenheimer, Report 51, 1918, page 1239). However, the corresponding 2-aminonaplithalin-1-carboxylic acid cannot be prepared from β-naphthisatin by this process.

     The observation has now been made that the preparation of 2-aminonaplithalin-1-carboxylic acid from β-naphthisatin can be accomplished in a smooth manner if the action of oxidizing agents, such as hydrogen peroxide, is carried out in an alkaline solution in the heat. Unexpectedly, this somewhat violent treatment did not attack the amidated compound in any way, and that could not be seen beforehand.

   The 2-amino-naphthalene-1-carboxylic acid is a. important intermediate product for the manufacture of dyes and pharmaceutical prod ucts, and their smooth production means a technical advance.- Example: 6 parts of ss-naphthisatin are dissolved in 45 parts of water and 15 parts of 40 'B6 sodium hydroxide solution and added to the boiling point Lö solution gradually as much of a solution of 12 parts of hydrogen peroxide 30% in twice the volume of water was added until a sample with dilute hydrochloric acid no longer separates red flakes. When doing this, ensure a spacious container and good stirring.

   It is then filtered and the solution is made acidic to the Congo with hydrochloric acid. The 2-aminonaphthalin-1-carboxylic acid separates out in a pale yellow color and can easily be completely purified by dissolving. The yield is about 90%.
EMI0002.0001
  
    If <SEP> one uses <SEP> at <SEP> place <SEP> of <SEP> 12 <SEP> parts
<tb> - \ @ 'asserstoffsuperozy <SEP> d <SEP> a <SEP> equivalent <SEP> amount
<tb> Persalts, <SEP> e.g. <SEP> B. <SEP> sodium superoxide <SEP> or <SEP> sodium perborate, <SEP> so <SEP> <SEP> you get <SEP> a <SEP> pale
<tb> result.

Claims (1)

EMI0002.0002 PATENTANSPRUCH: <tb> Verfahren <SEP> zur <SEP> Darstellung <SEP> von <SEP> n-Amino naplithalin-l-harbonsiiitre, <SEP> dadurch <SEP> gekenn- EMI0002.0003 zeichnet, <SEP> dass <SEP> man <SEP> p)-Naphthisatin <SEP> in <SEP> Geben wart <SEP> von <SEP> Alkalien <SEP> in <SEP> der <SEP> Ritze <SEP> mit <SEP> Oxyd:i t:ionsmitteln <SEP> behandelt. EMI0002.0002 PATENT CLAIM: <tb> Method <SEP> for <SEP> representation <SEP> of <SEP> n-amino naplithalin-l-harbonsiiitre, <SEP> thereby identifies <SEP> EMI0002.0003 draws, <SEP> that <SEP> man <SEP> p) -naphthisatin <SEP> in <SEP> Enter wa <SEP> of <SEP> alkalis <SEP> in <SEP> the <SEP> crack <SEP> with <SEP> Oxyd: it: ionizing agents <SEP> treated.
CH115109D 1926-06-01 1925-03-13 Process for the preparation of 2-aminonaphthalene-1-carboxylic acid. CH115109A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH115109T 1926-06-01

Publications (1)

Publication Number Publication Date
CH115109A true CH115109A (en) 1926-06-01

Family

ID=4374178

Family Applications (1)

Application Number Title Priority Date Filing Date
CH115109D CH115109A (en) 1926-06-01 1925-03-13 Process for the preparation of 2-aminonaphthalene-1-carboxylic acid.

Country Status (1)

Country Link
CH (1) CH115109A (en)

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