CH306508A - Process for the preparation of 2-cyclopentenyl acetic acid hydrazide. - Google Patents

Process for the preparation of 2-cyclopentenyl acetic acid hydrazide.

Info

Publication number
CH306508A
CH306508A CH306508DA CH306508A CH 306508 A CH306508 A CH 306508A CH 306508D A CH306508D A CH 306508DA CH 306508 A CH306508 A CH 306508A
Authority
CH
Switzerland
Prior art keywords
acetic acid
cyclopentenyl
hydrazine
soluble
acid hydrazide
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft V Siegfried
Original Assignee
Vormals B Siegfried 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 Vormals B Siegfried Ag filed Critical Vormals B Siegfried Ag
Publication of CH306508A publication Critical patent/CH306508A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/30—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C07C243/32—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

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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   42-Cyclopentenyl-essigsäurehydrazid.   



   Es wurde gefunden, dass das Hydrazid der   A2-Cyclopentenyl-essigsä. ure therapeutisch    wertvolle,   tuberkulostatische    Eigenschaften besitzt, und dass man diese bisher unbekannte Verbindung leicht dadurch herstellen kann, dass man eine die Gruppe
EMI1.1     
 enthaltende Verbindung mit Hydrazin bzw. dessen Salzen umsetzt. Das auf diese Weise    gewonnene #2-Cyclopentenyl-essigsäurehydra-    zid kristallisiert in farblosen feinen Nadeln, die einen   Schmelzpunkt von 75-76     C aufweisen und in Wasser und Alkohol leicht, in Äther und   Petroläther    wenig löslic sind.



   Beispiel :
154, 2 g   d2-Cyelopentenyl-essigsäure-athyl-    ester bzw. 144, 5   g #2-Cyclopentenyl-essigsäure-    chlorid werden mit 45 g Hydrazin bzw. 75 g Hydrazinhydrat versetzt und einige Stunden auf dem   Dampfbade    erhitzt. Nach dem Verjagen des   iibersehiissigen    Hydrazins erstarrt das   d2-Cyclopentenyl-essigsäurehydrazid. Es    wird gereinigt durch Umkristallisation aus Hexan oder Benzol oder durch Destillation.



   Das   d2-Cyclopentenyl-essigsäurehydrazid    bildet feine, verfilzte, farblose   Nädelchen    vom Schmelzpunkt 75-76  C. Siedepunkt 162  C bei 11 mm Druck.



   Das Produkt ist sehr   leiebt      loslich      in Was-    ser, Alkohol und Dioxan, wenig löslich in   licher    und Petroläther.  



   PATENTANSPRUCH :
Verfahren zur Darstellung von   #2-Cyclo-    pentenyl-essigsäurehydrazid, dadurch gekennzeichnet, dass man eine die Gruppe
EMI1.2     
   enthaltendeVerbindungauf    Hydrazin oder ein   Hydrazinsalz    einwirken lässt.



   Die neue Verbindung kristallisiert in farblosen feinen Nadeln, die einen Sehmelzpunkt von 75-76  C aufweisen und in Wasser und Alkohol leicht, in   Ather    und   Petrolather    wenig   loslich    sind. 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.





  



  Process for the preparation of 42-cyclopentenyl acetic acid hydrazide.



   It was found that the hydrazide of A2-cyclopentenyl-acetic acid. Has very therapeutically valuable, tuberculostatic properties, and that this previously unknown connection can easily be established by joining the group
EMI1.1
 containing compound reacts with hydrazine or its salts. The # 2-cyclopentenyl-acetic acid hydrazide obtained in this way crystallizes in colorless, fine needles which have a melting point of 75-76 ° C. and are easily soluble in water and alcohol, but not very soluble in ether and petroleum ether.



   Example:
154.2 g of d2-cyelopentenyl acetic acid ethyl ester or 144.5 g of # 2-cyclopentenyl acetic acid chloride are mixed with 45 g of hydrazine or 75 g of hydrazine hydrate and heated on the steam bath for a few hours. After the excess hydrazine has been driven off, the d2-cyclopentenyl-acetic acid hydrazide solidifies. It is purified by recrystallization from hexane or benzene or by distillation.



   The d2-cyclopentenyl-acetic acid hydrazide forms fine, matted, colorless needles with a melting point of 75-76 C. Boiling point 162 C at 11 mm pressure.



   The product is very easily soluble in water, alcohol and dioxane, but not very soluble in light and petroleum ether.



   PATENT CLAIM:
Process for the preparation of # 2-Cyclo-pentenyl-acetic acid hydrazide, characterized in that one the group
EMI1.2
   containing compound is allowed to act on hydrazine or a hydrazine salt.



   The new compound crystallizes in colorless, fine needles which have a melting point of 75-76 C and are easily soluble in water and alcohol, but not very soluble in ether and petroleum ether.

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Darstellung von 42-Cyclopentenyl-essigsäurehydrazid. Process for the preparation of 42-cyclopentenyl acetic acid hydrazide. Es wurde gefunden, dass das Hydrazid der A2-Cyclopentenyl-essigsä. ure therapeutisch wertvolle, tuberkulostatische Eigenschaften besitzt, und dass man diese bisher unbekannte Verbindung leicht dadurch herstellen kann, dass man eine die Gruppe EMI1.1 enthaltende Verbindung mit Hydrazin bzw. dessen Salzen umsetzt. Das auf diese Weise gewonnene #2-Cyclopentenyl-essigsäurehydra- zid kristallisiert in farblosen feinen Nadeln, die einen Schmelzpunkt von 75-76 C aufweisen und in Wasser und Alkohol leicht, in Äther und Petroläther wenig löslic sind. It was found that the hydrazide of A2-cyclopentenyl-acetic acid. Has very therapeutically valuable, tuberculostatic properties, and that this previously unknown connection can easily be established by joining the group EMI1.1 containing compound reacts with hydrazine or its salts. The # 2-cyclopentenyl-acetic acid hydrazide obtained in this way crystallizes in colorless, fine needles which have a melting point of 75-76 ° C. and are easily soluble in water and alcohol, but not very soluble in ether and petroleum ether. Beispiel : 154, 2 g d2-Cyelopentenyl-essigsäure-athyl- ester bzw. 144, 5 g #2-Cyclopentenyl-essigsäure- chlorid werden mit 45 g Hydrazin bzw. 75 g Hydrazinhydrat versetzt und einige Stunden auf dem Dampfbade erhitzt. Nach dem Verjagen des iibersehiissigen Hydrazins erstarrt das d2-Cyclopentenyl-essigsäurehydrazid. Es wird gereinigt durch Umkristallisation aus Hexan oder Benzol oder durch Destillation. Example: 154.2 g of d2-cyelopentenyl acetic acid ethyl ester or 144.5 g of # 2-cyclopentenyl acetic acid chloride are mixed with 45 g of hydrazine or 75 g of hydrazine hydrate and heated on the steam bath for a few hours. After the excess hydrazine has been driven off, the d2-cyclopentenyl-acetic acid hydrazide solidifies. It is purified by recrystallization from hexane or benzene or by distillation. Das d2-Cyclopentenyl-essigsäurehydrazid bildet feine, verfilzte, farblose Nädelchen vom Schmelzpunkt 75-76 C. Siedepunkt 162 C bei 11 mm Druck. The d2-cyclopentenyl-acetic acid hydrazide forms fine, matted, colorless needles with a melting point of 75-76 C. Boiling point 162 C at 11 mm pressure. Das Produkt ist sehr leiebt loslich in Was- ser, Alkohol und Dioxan, wenig löslich in licher und Petroläther. The product is very easily soluble in water, alcohol and dioxane, but not very soluble in light and petroleum ether. PATENTANSPRUCH : Verfahren zur Darstellung von #2-Cyclo- pentenyl-essigsäurehydrazid, dadurch gekennzeichnet, dass man eine die Gruppe EMI1.2 enthaltendeVerbindungauf Hydrazin oder ein Hydrazinsalz einwirken lässt. PATENT CLAIM: Process for the preparation of # 2-Cyclo-pentenyl-acetic acid hydrazide, characterized in that one the group EMI1.2 containing compound is allowed to act on hydrazine or a hydrazine salt. Die neue Verbindung kristallisiert in farblosen feinen Nadeln, die einen Sehmelzpunkt von 75-76 C aufweisen und in Wasser und Alkohol leicht, in Ather und Petrolather wenig loslich sind. The new compound crystallizes in colorless, fine needles which have a melting point of 75-76 C and are easily soluble in water and alcohol, but not very soluble in ether and petroleum ether.
CH306508D 1952-06-19 1952-06-19 Process for the preparation of 2-cyclopentenyl acetic acid hydrazide. CH306508A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH306508T 1952-06-19

Publications (1)

Publication Number Publication Date
CH306508A true CH306508A (en) 1955-04-15

Family

ID=4492842

Family Applications (1)

Application Number Title Priority Date Filing Date
CH306508D CH306508A (en) 1952-06-19 1952-06-19 Process for the preparation of 2-cyclopentenyl acetic acid hydrazide.

Country Status (1)

Country Link
CH (1) CH306508A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3072706A (en) * 1960-09-08 1963-01-08 Cyclopentenyl cyclopenteneacetic acid and derivatives
EP0323590A2 (en) * 1987-12-24 1989-07-12 Ono Pharmaceutical Co., Ltd. Carbazoyl derivatives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3072706A (en) * 1960-09-08 1963-01-08 Cyclopentenyl cyclopenteneacetic acid and derivatives
EP0323590A2 (en) * 1987-12-24 1989-07-12 Ono Pharmaceutical Co., Ltd. Carbazoyl derivatives
EP0323590A3 (en) * 1987-12-24 1990-05-02 Ono Pharmaceutical Co., Ltd. Carbazoyl derivatives

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