CH205417A - Process for the preparation of 1- (4'-nitro-2'-aldehydophenoxy) -6-acetylaminonaphthalene-3-sulfonic acid. - Google Patents

Process for the preparation of 1- (4'-nitro-2'-aldehydophenoxy) -6-acetylaminonaphthalene-3-sulfonic acid.

Info

Publication number
CH205417A
CH205417A CH205417DA CH205417A CH 205417 A CH205417 A CH 205417A CH 205417D A CH205417D A CH 205417DA CH 205417 A CH205417 A CH 205417A
Authority
CH
Switzerland
Prior art keywords
sulfonic acid
nitro
aldehydophenoxy
preparation
acetylaminonaphthalene
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH205417A publication Critical patent/CH205417A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups

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

Description

  

  Verfahren zur Darstellung von     1-(4'-Nitro-2'-aldehydophenogy)-6-          acetylaminonaphthalin-3-sulfonsäure.       Es wurde gefunden, dass durch Umset  zung des     Dinatriumsalzes    der     2-Acetylamino-          5-oxynaphthalin-7-sulfonsäure    mit     2-Chlor-          5-nitrobenzaldehyd    in sehr guter Ausbeute  1 - (4'-     Nitro    - 2'-     aldehydophenoxy)-6-acetyl-          aminonaphthalin-3-sulfonsäure    entsteht.

   Die  neue Verbindung ist als     Natriumsalz    in Was  ser löslich, färbt sich mit konzentrierter  Schwefelsäure intensiv orangegelb und gibt  ein     gelboranges        Hydrazon.    Sie soll als Zwi  schenprodukt in der     Farbstoffindustrie    Ver  wendung finden.  



       Beispiel:     Das aus 47,8 kg     2-Amino-5-oxynaphtha-          lin-7-sulfonsäure    bereitete     Mononatriumsalz     des     N-Acetylderivates    wird in der     Acetylie-          rungslösung    mit soviel Natronlauge versetzt,  dass eben     ätzalkalische    Reaktion     eintritt    und  diese mit einer Spur Mineralsäure entfernt.  Alsdann fügt man 37 kg     2-Chlor-5-nitro-          benzaldehyd    zu und kocht unter Rühren und       Rückfluss    etwa 50 Stunden.

   Aus der filtrier-         ten    Lösung wird die     1-(4'-Nitro-2'-aldehydo-          phenoxy)    - 6 -     acetylaminonaphthalin-3-sulf        on-          säure    durch Kochsalz gefällt, filtriert     und     durch mehrmaliges     Umlösen    und     Aussalzen     gereinigt.

   Diese     Aldehydsulfonsäure    ist als       Natriumsalz        in    Wasser löslich, färbt sich  mit konzentrierter Schwefelsäure intensiv  orangegelb und gibt ein     gelboranges-        Hydra-          zon.  



  Process for the preparation of 1- (4'-nitro-2'-aldehydophenogy) -6-acetylaminonaphthalene-3-sulfonic acid. It has been found that by reacting the disodium salt of 2-acetylamino-5-oxynaphthalene-7-sulfonic acid with 2-chloro-5-nitrobenzaldehyde in very good yield 1 - (4'-nitro-2'-aldehydophenoxy) -6- acetyl aminonaphthalene-3-sulfonic acid is formed.

   The new compound is soluble in water as the sodium salt, turns an intense orange-yellow with concentrated sulfuric acid and gives a yellow-orange hydrazone. It should be used as an intermediate product in the dye industry.



       Example: The monosodium salt of the N-acetyl derivative prepared from 47.8 kg of 2-amino-5-oxynaphthalin-7-sulfonic acid is mixed with enough sodium hydroxide solution in the acetylation solution that an alkaline reaction occurs and this is removed with a trace of mineral acid . 37 kg of 2-chloro-5-nitrobenzaldehyde are then added and the mixture is refluxed for about 50 hours while stirring.

   The 1- (4'-nitro-2'-aldehydophenoxy) - 6 - acetylaminonaphthalene-3-sulfonic acid is precipitated from the filtered solution with common salt, filtered and purified by repeated dissolution and salting out.

   This aldehyde sulfonic acid is soluble in water as the sodium salt, turns an intense orange-yellow color with concentrated sulfuric acid and gives a yellow-orange hydrazone.

Claims (1)

PATENTANSPRUCH: Verfahren zurDarstellung von 1-(4'-Nitro- 2' - aldehydophenoxy)-6-acetylaminonaphtha- lin-3-sulfonsäure, dadurch gekennzeichnet, dass man das Dinatriumsalz der 2-Acetyl- amino-5-oxynaphthalin-7-sulfonsäure mit 2- Chlor-5-nitrobenzaldehyd umsetzt. PATENT CLAIM: Process for the preparation of 1- (4'-nitro- 2 '- aldehydophenoxy) -6-acetylaminonaphthalin-3-sulfonic acid, characterized in that the disodium salt of 2-acetylamino-5-oxynaphthalene-7-sulfonic acid reacted with 2-chloro-5-nitrobenzaldehyde. Die neue Verbindung ist als Natriumsalz in Wasser löslich, färbt sich mit konzentrieterSchwefel- säure intensiv orangegelb und gibt ein gelb oranges Hydrazon. The new compound is soluble in water as the sodium salt, turns an intense orange-yellow with concentrated sulfuric acid and gives a yellow-orange hydrazone.
CH205417D 1936-02-29 1936-12-04 Process for the preparation of 1- (4'-nitro-2'-aldehydophenoxy) -6-acetylaminonaphthalene-3-sulfonic acid. CH205417A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE205417X 1936-02-29
CH193922T 1936-12-04

Publications (1)

Publication Number Publication Date
CH205417A true CH205417A (en) 1939-06-15

Family

ID=25722609

Family Applications (1)

Application Number Title Priority Date Filing Date
CH205417D CH205417A (en) 1936-02-29 1936-12-04 Process for the preparation of 1- (4'-nitro-2'-aldehydophenoxy) -6-acetylaminonaphthalene-3-sulfonic acid.

Country Status (1)

Country Link
CH (1) CH205417A (en)

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