DE909938C - Process for the preparation of 2-oxy-4- (ªÏ-amino-methyl) -benzoic acid - Google Patents

Process for the preparation of 2-oxy-4- (ªÏ-amino-methyl) -benzoic acid

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Publication number
DE909938C
DE909938C DEC5059A DEC0005059A DE909938C DE 909938 C DE909938 C DE 909938C DE C5059 A DEC5059 A DE C5059A DE C0005059 A DEC0005059 A DE C0005059A DE 909938 C DE909938 C DE 909938C
Authority
DE
Germany
Prior art keywords
oxy
benzoic acid
amino
methyl
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
DEC5059A
Other languages
German (de)
Inventor
Dr Wilhelm Kunze
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur 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 Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEC5059A priority Critical patent/DE909938C/en
Application granted granted Critical
Publication of DE909938C publication Critical patent/DE909938C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton

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

Description

Verfahren zur Herstellung von 2-Oxy-4-(a)-amino-methyl)-benzoesäure In -Berichte der Deutschen Chemischen Gesellschaft«, Bd. 83 (195o), S. 304, ist ein Verfahren zur Herstellung von 2-Oxy-4-(o)-amino-methyl)-benzoesäure beschrieben. Hiernach wird diese Verbindung durch Hydrierung von 4-Cvan-2-oxy-benzoesäure hergestellt. Diese Methode eignet sich jedoch nicht zur technischen Herstellung der 2-Oxy-4-(co-amino-methyl)-benzoesäure, da das Ausgangsmaterial dieses Verfahrens, die 4-Cyan-2-oxy-benzoesäure technisch nur mit geringen Ausbeuten erhalten werden kann.Process for the preparation of 2-oxy-4- (a) -amino-methyl) -benzoic acid In reports of the German Chemical Society, Vol. 83 (195o), p. 304, is a process for the preparation of 2-oxy-4- (o) -amino-methyl) -benzoic acid described. This compound is then prepared by hydrogenating 4-Cvan-2-oxy-benzoic acid. However, this method is not suitable for the industrial production of 2-oxy-4- (co-amino-methyl) -benzoic acid, as the starting material of this process, 4-cyano-2-oxy-benzoic acid technical can only be obtained with low yields.

Es wurde nun gefunden, daß man 2-Oxy-4-(o)-amino-methyl)-benzoesäure in einfacher Weise erhalten kann, wenn man auf 3-Oxy-benzylamin Kohlendioxyd in Gegenwart von Alkalicarbonat bei erhöhter Temperatur und erhöhtem Druck einwirken läßt. Die Anwendung inerter Verdünnungsmittel, wie Graphit, ist dabei zweckmäßig.It has now been found that 2-oxy-4- (o) -amino-methyl) -benzoic acid can be obtained in a simple manner if you rely on 3-oxy-benzylamine carbon dioxide in Act in the presence of alkali carbonate at elevated temperature and pressure leaves. It is advisable to use inert diluents such as graphite.

Das hier als Ausgangsmaterial verwendete 3-Oxybenzylamin ist z. B. durch katalytische Hydrierung von 3-Oxybenzonitril herstellbar.The 3-oxybenzylamine used here as a starting material is z. B. can be prepared by catalytic hydrogenation of 3-oxybenzonitrile.

Die 2-Oxy-4-(co-amino-methyl)-benzoesäure stellt ein wertvolles Zwischenprodukt zur Herstellung von Farbstoffen und Heilmitteln sowie selbst ein Heilmittel dar. Beispiel 4o Teile 3-Oxybenzy lamin werden mit 12o Teilen trockenem Kaliumcarbonat, 24o Teilen trockenem Flockengraphit, 5 Teilen Zinkstaub innig vermischt und in einem Druckgefäß unter Einbringen von Kohlendioxyd unter einem Druck von 3o at und unter Rühren auf 18o° erhitzt. Man erhöht den Druck auf 6o at und rührt noch 3 Stunden bei r8o°. Nach dem Erkalten wird das Reaktionsprodukt mit Wasser und anschließend mit verdünnter Natronlauge ausgezogen; die vereinigten, eingeengten Filtrate werden mit Säure neutral gestellt, wobei die entstandene a-Oxy-q.-(co-amino-methyl)-benzoesäure sich abscheidet. Nach dem Umkristallisieren aus Wasser zeigt das Produkt die in der Literatur angegebenen Eigenschaften.2-Oxy-4- (co-amino-methyl) -benzoic acid is a valuable intermediate for the production of dyes and remedies as well as a remedy itself. Example 4o parts of 3-Oxybenzy lamin are mixed with 12o parts of dry potassium carbonate, 24o parts of dry flake graphite, 5 parts of zinc dust intimately mixed and in one Pressure vessel with the introduction of Carbon dioxide under a pressure of 30 at and heated to 180 ° with stirring. The pressure is increased to 60 atm and stirred another 3 hours at r8o °. After cooling, the reaction product is mixed with water and then extracted with dilute sodium hydroxide solution; the united, narrowed Filtrates are made neutral with acid, the resulting α-oxy-q .- (co-aminomethyl) benzoic acid separates. After recrystallization from water, the product shows the in properties given in the literature.

Das hier verwendete 3-Oxybenzylamin kann z. B. durch Diazotieren und Verkochen des 3-Amino-benzonitrils und katalytische Hydrierung des so gebildeten 3-Oxybenzonitrils als eine bei x68° schmelzende Substanz erhalten werden.The 3-oxybenzylamine used here can, for. B. by diazotization and Boiling the 3-amino-benzonitrile and catalytic hydrogenation of the so formed 3-oxybenzonitrile can be obtained as a substance melting at x68 °.

Claims (1)

PATENTANSPRUCH: Verf ahren zur Herstellung von a-Oxy-q.-(o)-aminomethyl)-benzoesäure, dadurch gekennzeichnet, daß man 3-Oxybenzylamin bei Gegenwart von Alkalicarbonaten bei erhöhter Temperatur und unter erhöhtem Druck mit Kohlendioxyd behandelt und das Reaktionsprodukt mit Säure neutral stellt.PATENT CLAIM: Process for the production of a-Oxy-q .- (o) -aminomethyl) -benzoic acid, characterized in that 3-oxybenzylamine in the presence of alkali carbonates treated with carbon dioxide at elevated temperature and under elevated pressure and makes the reaction product neutral with acid.
DEC5059A 1951-12-05 1951-12-05 Process for the preparation of 2-oxy-4- (ªÏ-amino-methyl) -benzoic acid Expired DE909938C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC5059A DE909938C (en) 1951-12-05 1951-12-05 Process for the preparation of 2-oxy-4- (ªÏ-amino-methyl) -benzoic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC5059A DE909938C (en) 1951-12-05 1951-12-05 Process for the preparation of 2-oxy-4- (ªÏ-amino-methyl) -benzoic acid

Publications (1)

Publication Number Publication Date
DE909938C true DE909938C (en) 1954-04-26

Family

ID=7013571

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC5059A Expired DE909938C (en) 1951-12-05 1951-12-05 Process for the preparation of 2-oxy-4- (ªÏ-amino-methyl) -benzoic acid

Country Status (1)

Country Link
DE (1) DE909938C (en)

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