CH307873A - Process for the preparation of a new isoquinoline compound. - Google Patents

Process for the preparation of a new isoquinoline compound.

Info

Publication number
CH307873A
CH307873A CH307873DA CH307873A CH 307873 A CH307873 A CH 307873A CH 307873D A CH307873D A CH 307873DA CH 307873 A CH307873 A CH 307873A
Authority
CH
Switzerland
Prior art keywords
isoquinoline
preparation
new
compound
hydrazine
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH307873A publication Critical patent/CH307873A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring

Landscapes

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

Description

  

  verfahren     zur    Herstellung einer neuen     Isochinolinverbindung.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen       Hydrazons,    das dadurch gekennzeichnet ist,       da.ss    man eine Verbindung der Formel  
EMI0001.0005     
    worin X einen     austai-isehfähigen        Substituen-          ten,    z.

   B. eine     veresterte        Oxygruppe,    beson  ders ein Halogenatom, oder eine     Phenoxy-          oder        Thioäthergruppe,    bedeutet, mit     Hydrazin     und das erhaltene     1-Hydrazino-isochinolin    mit       Aeeton    umsetzt.  



  Das so erhaltene     1-Isopropyliden-2-isoehi-          nolyl-(1')-hydrazin    ist neu und schmilzt bei  1.05-106 ; es zeigt eine ausgeprägte und  langandauernde blutdrucksenkende Wirkung  und soll als Heilmittel Verwendung finden.       Beispiel:     10 Gewichtsteile     1-Chlor-isochinolin    wer  den in einem Gemisch von 25     Volumteilen          Hydrazinhydrat    und 50     Volumteilen    Äthyl  alkohol während 6 Stunden im geschlossenen  Gefäss auf 100-110  erhitzt. Nach dem Er  kalten saugt man von dem in filzigen Nadeln  auskristallisierten Reaktionsprodukt ab.

   Es    besteht aus schon fast reinem     1-Hydrazino-          isochinolin    der Formel  
EMI0001.0026     
    Die freie Base lässt sich zur völligen Rei  nigung aus Essigester     um-kristallisieren    und       schmilzt    dann bei etwa 172 . Das salzsaure       Salz    erhält man durch Auflösen von I Ge  wichtsteil     1-Hydrazino-isochinolin    in 10     Vo-          lumteilen        2n-HCl    in der Hitze und Auskri  stallisieren beim Abkühlen. Es lässt sieh aus       Äthylalkohol        umkristallisieren    und schmilzt  dann bei 247-248 .  



  2 Gewichtsteile der freien Base     werden    in  25     Volumteilen        2n-Natriumacetatlösung    gelöst  und mit 2     Volumteilen    Aceton versetzt. Die  ölige     Abscheidung    wird beim Reiben kristal  lin und stellt das     1-Isopropyliden-2-isochino-          lyl-(1')-hydrazin    der Formel  
EMI0001.0043     
    dar, das, aus     Cyclohexan        umkristallisiert,    bei  105-106  schmilzt.



  process for the preparation of a new isoquinoline compound. The subject of the present patent is a process for the preparation of a new hydrazone, which is characterized in that a compound of the formula
EMI0001.0005
    where X is an exchangeable substituent, e.g.

   B. an esterified oxy group, FITS a halogen atom, or a phenoxy or thioether group, means with hydrazine and the 1-hydrazino-isoquinoline obtained is reacted with acetone.



  The 1-isopropylidene-2-isoehi- nolyl- (1 ') - hydrazine obtained in this way is new and melts at 1.05-106; it shows a pronounced and long-lasting antihypertensive effect and is said to be used as a remedy. Example: 10 parts by weight of 1-chloro-isoquinoline who is heated in a mixture of 25 parts by volume of hydrazine hydrate and 50 parts by volume of ethyl alcohol for 6 hours in a closed vessel to 100-110. After the cold he sucks off the reaction product which has crystallized out in felt needles.

   It consists of almost pure 1-hydrazinoisoquinoline of the formula
EMI0001.0026
    The free base can be recrystallized from ethyl acetate for complete purification and then melts at about 172. The hydrochloric acid salt is obtained by dissolving 1 part by weight of 1-hydrazino-isoquinoline in 10 parts by volume of 2N HCl in the heat and crystallizing out on cooling. It can be recrystallized from ethyl alcohol and then melts at 247-248.



  2 parts by weight of the free base are dissolved in 25 parts by volume of 2N sodium acetate solution, and 2 parts by volume of acetone are added. The oily deposit becomes crystalline when rubbed and represents 1-isopropylidene-2-isoquinolyl- (1 ') - hydrazine of the formula
EMI0001.0043
    which, recrystallized from cyclohexane, melts at 105-106.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer neuen Isochinolinverbindung, dadurch gekennzeich net, dass man eine Verbindung der Formel EMI0002.0002 worin X einen austauschfähigen Substituen- ten bedeutet, mit Hydrazin und das erhaltene 1.-Hydrazino-isochinolin mit Aceton umsetzt. Das so erhaltene 1-IsopropyIiden-2-isochi- nolyl-(1')-hydrazin ist neu und schmilzt. bei 105-106 . Es zeigt eine ausgeprägte und langandauernde blutdrucksenkende Wirkung und soll als Heilmittel Verwendung finden. UNTERANSPRÜCHE: 1. PATENT CLAIM: Process for the preparation of a new isoquinoline compound, characterized in that a compound of the formula EMI0002.0002 where X is an exchangeable substituent with hydrazine and the 1.-hydrazino-isoquinoline obtained is reacted with acetone. The 1-isopropyliden-2-isoquinolyl (1 ') hydrazine obtained in this way is new and melts. at 105-106. It shows a pronounced and long-lasting antihypertensive effect and is said to be used as a remedy. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, da.ss man ein Isochino- lin, das in 1-Stellung eine veresterte Oxy- gruppe enthält, als Ausgangsstoff verwendet. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man ein 1-Halogen-isochinolin verwendet. Process according to patent claim, characterized in that an isoquinoline which contains an esterified oxy group in the 1-position is used as the starting material. 2. The method according to claim and dependent claim 1, characterized in that a 1-halo-isoquinoline is used.
CH307873D 1952-05-30 1952-05-30 Process for the preparation of a new isoquinoline compound. CH307873A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH307873T 1952-05-30
CH301952T 1952-05-30

Publications (1)

Publication Number Publication Date
CH307873A true CH307873A (en) 1955-06-15

Family

ID=25734453

Family Applications (1)

Application Number Title Priority Date Filing Date
CH307873D CH307873A (en) 1952-05-30 1952-05-30 Process for the preparation of a new isoquinoline compound.

Country Status (1)

Country Link
CH (1) CH307873A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4473501A (en) * 1981-05-04 1984-09-25 G. D. Searle & Co. Dihydro azino isoquinolines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4473501A (en) * 1981-05-04 1984-09-25 G. D. Searle & Co. Dihydro azino isoquinolines

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