DE447303C - Process for the preparation of 2-oxypyridine-5-carboxylic acid - Google Patents

Process for the preparation of 2-oxypyridine-5-carboxylic acid

Info

Publication number
DE447303C
DE447303C DER62506D DER0062506D DE447303C DE 447303 C DE447303 C DE 447303C DE R62506 D DER62506 D DE R62506D DE R0062506 D DER0062506 D DE R0062506D DE 447303 C DE447303 C DE 447303C
Authority
DE
Germany
Prior art keywords
oxypyridine
carboxylic acid
preparation
cyanopyridine
saponification
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
DER62506D
Other languages
German (de)
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to DER62506D priority Critical patent/DE447303C/en
Application granted granted Critical
Publication of DE447303C publication Critical patent/DE447303C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Verfahren zur Herstellung von 2-Oxypyridin-5-carbonsäure. Bei der Verseifung von Cyanderivaten entstehen im allgemeinen die entsprechenden Carbonsäuren, ohne daß hierbei andere vorhandene Substituenten des Moleküls eine Veränderung erfahren.Process for the preparation of 2-oxypyridine-5-carboxylic acid. In the Saponification of cyan derivatives generally results in the corresponding carboxylic acids, without that other existing substituents of the molecule undergo a change.

Es wurde nun gefunden, daß überraschenderweise bei der Verseifung des 2-Chlor-5-cyanpyridins nicht nur die Cyangruppe zur Carboxylgruppe verseift, sondern gleichzeitig das Halogenatom durch die Hydroxylgruppe ersetzt wird.It has now been found that, surprisingly, during the saponification of the 2-chloro-5-cyanopyridine not only saponifies the cyano group to the carboxyl group, but at the same time the halogen atom is replaced by the hydroxyl group.

Die Verseifung kann hierbei mit alkalischen oder sauren Mitteln erfolgen. Beispiele. i. io g 2-Chlor-5-cyanpyridin werden mit i io ccm einer 2oprozentigen alkoholischen Lösung von Ätznatron längere Zeit im geschlossenen Gefäß auf Temperaturen über ioo` erhitzt.The saponification can be done with alkaline or acidic agents. Examples. i. 10 g of 2-chloro-5-cyanopyridine are added with 10 ccm of a 2% strength Alcoholic solution of caustic soda for a long time in a closed vessel at temperatures heated over ioo`.

Das Reaktionsgemisch wird dann mit Wasser verdünnt und mit Salzsäure kongosauer gemacht. Hierbei scheidet sich die 2-Oxypyridin-5-carbonsäure als feinkristallinischer Niederschlag ab. Nach dem Umkristallisieren aus Essigsäure zeigt die Verbindung einen Schmelzpunkt von 3o2 bis 3o3°.The reaction mixture is then diluted with water and with hydrochloric acid made Congo sour. Here, the 2-oxypyridine-5-carboxylic acid separates as a finely crystalline one Precipitation from. After recrystallization from acetic acid, the compound shows a melting point of 3o2 to 3o3 °.

2. 3 g 2-Chlor-5-cyanpyridin werden mit ioccm konzentrierter Salzsäure (Dichte: i,19) im Bombenrohr auf i 5o° erhitzt. Der Rohrinhalt wird alsdann in Sodalösung gelöst,, durch Zusatz von Salzsäure fällt die 2-Oxypyridin-5-carbonsäure aus. Die Ausbeute ist annähernd quantitativ.2. 3 g of 2-chloro-5-cyanopyridine are mixed with 10 cm of concentrated hydrochloric acid (Density: 1.19) heated to 150 ° in a bomb tube. The pipe contents are then in soda solution dissolved, by adding hydrochloric acid, the 2-oxypyridine-5-carboxylic acid precipitates. the The yield is almost quantitative.

Die 2-Oxypyridin-5-carbonsäure kann als solche sowie als Ausgangsstoff für die Darstellung anderer therapeutisch wichtiger Verbindungen Verwendung finden.The 2-oxypyridine-5-carboxylic acid can be used as such and as a starting material find use for the representation of other therapeutically important compounds.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung der 2-Oxypyridin-5-carbonsäure, dadurch gekennzeichnet, daß 2-Halogen-5-cyanpyridin mit verseifenden Mitteln behandelt wird.PATENT CLAIM: Process for the preparation of 2-oxypyridine-5-carboxylic acid, characterized in that 2-halo-5-cyanopyridine is treated with saponifying agents will.
DER62506D 1924-11-12 1924-11-12 Process for the preparation of 2-oxypyridine-5-carboxylic acid Expired DE447303C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DER62506D DE447303C (en) 1924-11-12 1924-11-12 Process for the preparation of 2-oxypyridine-5-carboxylic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER62506D DE447303C (en) 1924-11-12 1924-11-12 Process for the preparation of 2-oxypyridine-5-carboxylic acid

Publications (1)

Publication Number Publication Date
DE447303C true DE447303C (en) 1927-07-23

Family

ID=7411942

Family Applications (1)

Application Number Title Priority Date Filing Date
DER62506D Expired DE447303C (en) 1924-11-12 1924-11-12 Process for the preparation of 2-oxypyridine-5-carboxylic acid

Country Status (1)

Country Link
DE (1) DE447303C (en)

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