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
Links
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)
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) |
-
1925
- 1925-03-13 CH CH115109D patent/CH115109A/en unknown
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