DE541171C - Process for the preparation of 1-oxy-2-rhodannaphthalene-3-carboxylic acid and its derivatives - Google Patents

Process for the preparation of 1-oxy-2-rhodannaphthalene-3-carboxylic acid and its derivatives

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Publication number
DE541171C
DE541171C DEI38101D DEI0038101D DE541171C DE 541171 C DE541171 C DE 541171C DE I38101 D DEI38101 D DE I38101D DE I0038101 D DEI0038101 D DE I0038101D DE 541171 C DE541171 C DE 541171C
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DE
Germany
Prior art keywords
carboxylic acid
derivatives
rhodannaphthalene
oxy
preparation
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEI38101D
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German (de)
Inventor
Dr Ernst Runne
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
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
Priority to DEI38101D priority Critical patent/DE541171C/en
Application granted granted Critical
Publication of DE541171C publication Critical patent/DE541171C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/14—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups

Description

Verfahren zur Darstellung von 1-Oxy-2-rhodannaphthalin-3-carbonsäure und ihren Derivaten Es wurde gefunden, daß i-Oxynaphthaän-3-carbonsäüre bei der Rhodanierung nicht in der q.-Stellung substituiert wird, sondern daß trotz der freien q.-Stellung der neue Substituent in die 2-Stellung eintritt. Dies war nicht vorauszusehen, da a-Naphthol in der 4-Stellung rhodäniert wird. Ebenso wie die i-Oxynaphthalin-3-carbonsäure verhalten sich auch ihre Derivate.Process for the preparation of 1-oxy-2-rhodannaphthalene-3-carboxylic acid and its derivatives It has been found that i-oxynaphthaene-3-carboxylic acid in the Rhodanation is not substituted in the q. Position, but that despite the free q.-position the new substituent enters the 2-position. This could not be foreseen because a-naphthol is rhodiumed in the 4-position. Just like the i-oxynaphthalene-3-carboxylic acid their derivatives behave too.

Daß die Rhodangruppe sich in der 2-Stellung befindet, folgt daraus, daß die aus der rhodanierten i-Oxynaphthalin-3-carbonsäure durch Reduzieren, Kondensieren mit Monochloressigsäure und Äthylieren dargestellte i-Äthoxynaphthalinthioglykolsäure-3-carbonsäure vom F. 158 bis 159' identisch ist mit der i-Äthoxynaphthahn-2-thioglykolsäure-3-carbonsäure, die durch Umsetzung von Thioglykolsäure mit r Äthoxy-2-chlornaphthalin-3-carbonsäure gewonnen wird. Diese i-Äthoxy-2-chlornaphtha lin-3-carbonsäure kann aus der i-Äthoxy-2-aminonaphthalin-3-carbonsäure durch Diazotieren und Einführen von Chlor nach Sand -m ey eroder durch Chlorieren von i-Oxynaphthalin-3-carbonsäure und Äthylieren dargestellt werden.The fact that the rhodan group is in the 2-position follows from the fact that the i-ethoxynaphthalenethioglycolic acid-3-carboxylic acid, prepared from the rhodanated i-oxynaphthalene-3-carboxylic acid by reducing, condensing with monochloroacetic acid and ethylating, is identical with a temperature of 158 to 159 ' is with i-ethoxynaphthane-2-thioglycolic acid-3-carboxylic acid, which is obtained by reacting thioglycolic acid with ethoxy-2-chloronaphthalene-3-carboxylic acid. This i-ethoxy-2-chloronaphtha lin-3-carboxylic acid can be obtained from i-ethoxy-2-aminonaphthalene-3-carboxylic acid by diazotizing and introducing chlorine to S an d -m ey or by chlorinating i-oxynaphthalene-3- carboxylic acid and ethylation are represented.

Die Rhodanierung kann nach den dafür bekannten Verfahren durchgeführt werden. Die neuen Verbindungen sollen als Zwischenprodukte für Farbstoffe usw. verwendet werden.The rhodanation can be carried out by the processes known for this purpose will. The new compounds are said to be used as intermediates for dyes, etc. will.

Beispiele: i. 5o Gewichtsteile Kalium= rhodanid und ig Gewichtsteile i-Oxynaphthalin-3-carbonsäure werden in Methylalkohol gelöst. Man läßt unter Kühlung eine Mischung aus mit Natriumbromid gesättigtem Methylalkohol und io Raumteilen Brom zutropfen. Die in sehr guter Ausbeute entstehende Rhodanverbindung scheidet sich ab und wird nach einiger Zeit abgenutscht, mit Wasser gewaschen und z. B. aus Kaliumcarbonat umgelöst. - Sie- schmilzt dann bei 213 bis 2i5 ° unter Zersetzung. Die Analyse entspricht einer Monorhodanverbindung. Wird das Rohprodukt aus Alkohol umkristallisiert, so spaltet sich der Stickstoff ab. Es dürften hier ähnliche Verhältnisse vorliegen, wie sie im Arch. d. Pharm. 267 [i929], Seiten 203 und 211 bei der Rhodanierung des -p-Kresols geschildert sind.Examples: i. 50 parts by weight of potassium = rhodanide and ig parts by weight i-Oxynaphthalene-3-carboxylic acid are dissolved in methyl alcohol. It is left with cooling a mixture of methyl alcohol saturated with sodium bromide and 10 parts by volume Add bromine in drops. The rhodane compound formed in very good yield separates and is sucked off after a while, washed with water and z. B. off Dissolved potassium carbonate. - It then melts at 213 to 25 ° with decomposition. The analysis corresponds to a monorhodane compound. Becomes the raw product from alcohol recrystallized, the nitrogen is split off. Similar conditions are likely here exist as they are in Arch. d. Pharm. 267 [1929], pages 203 and 211 on rhodanization des -p-cresol are shown.

2. Ersetzt man in Beispiel i die i-Oxynaphthalin-3-carbonsäure durch 22 Gewichtsteile ihres Äthylesters, so wird eine Rhodanverbindung erhalten, die beim Umkriställisieren aus Alkohol ebenfalls ihren Stickstoff verliert und dann bei 136 bis i37° schmilzt. Der Schwefelgehalt dieser Verbindung entspricht der Formel "14H10045.2. Replace the i-oxynaphthalene-3-carboxylic acid in example i with 22 parts by weight of its ethyl ester, a rhodan compound is obtained which when recrystallizing from alcohol also loses its nitrogen and then melts at 136 to i37 °. The sulfur content of this compound corresponds to the formula "14H10045.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von i-Oxy-2-rhodannaphthalin-3-carbonsäure und ihren Derivaten, dadurch gekennzeichnet, da.ß man i-Oxynaphthalin-3-carbonsäure oder ihre Derivate rhodaniert.PATENT CLAIM: Process for the preparation of i-Oxy-2-rhodannaphthalene-3-carboxylic acid and their derivatives, characterized in that i-oxynaphthalene-3-carboxylic acid is used or their derivatives rhodium-plated.
DEI38101D 1929-05-22 1929-05-22 Process for the preparation of 1-oxy-2-rhodannaphthalene-3-carboxylic acid and its derivatives Expired DE541171C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI38101D DE541171C (en) 1929-05-22 1929-05-22 Process for the preparation of 1-oxy-2-rhodannaphthalene-3-carboxylic acid and its derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI38101D DE541171C (en) 1929-05-22 1929-05-22 Process for the preparation of 1-oxy-2-rhodannaphthalene-3-carboxylic acid and its derivatives

Publications (1)

Publication Number Publication Date
DE541171C true DE541171C (en) 1932-01-08

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ID=7189697

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI38101D Expired DE541171C (en) 1929-05-22 1929-05-22 Process for the preparation of 1-oxy-2-rhodannaphthalene-3-carboxylic acid and its derivatives

Country Status (1)

Country Link
DE (1) DE541171C (en)

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