CH302151A - Process for making an indole series ketone. - Google Patents

Process for making an indole series ketone.

Info

Publication number
CH302151A
CH302151A CH302151DA CH302151A CH 302151 A CH302151 A CH 302151A CH 302151D A CH302151D A CH 302151DA CH 302151 A CH302151 A CH 302151A
Authority
CH
Switzerland
Prior art keywords
sep
making
acetyl
indole
catalyst
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Sandoz
Original Assignee
Ag Sandoz
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 Ag Sandoz filed Critical Ag Sandoz
Publication of CH302151A publication Critical patent/CH302151A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles

Description

  

      Verfahren        zur        Herstellung    eines     Ketons    der     Indolreihe.     
EMI0001.0006     
  
    Es <SEP> wurde <SEP> gefunden, <SEP> dass <SEP> man <SEP> zu <SEP> N <SEP> Acetyl  aketo-1,2,2',3,4,5-hexahydro-benz(od),indo'1 <SEP> ge  lang4 <SEP> wenn <SEP> man <SEP> auf <SEP> ss-[1-Acetyl-4-carboxy  2,3-d-ihydro-indolyl <SEP> (3) <SEP> ] <SEP> -propionsäure <SEP> ein <SEP> Cy <SEP> -            clisierungsmittel    unter Verwendung eines     Ka-          talysators    einwirken lässt.

   Das folgende  Schema     veranschaulicht    die     Reaktion:     
EMI0001.0012     
  
EMI0001.0013     
  
    Zur <SEP> Ausführung <SEP> des <SEP> erfindungsgemässen
<tb>  Verfahrens <SEP> wird <SEP> zum <SEP> Beispiel <SEP> ss <SEP> [1-Acetyl  4-carboxy <SEP> - <SEP> 2,3 <SEP> - <SEP> dihydro <SEP> - <SEP> indolyl <SEP> (3) <SEP> ] <SEP> -propion  säure <SEP> und <SEP> Kaliiuncyanid <SEP> (Katalysator) <SEP> in
<tb>  Acetanhydrid <SEP> (Cyclisierungsmittel) <SEP> gelöst <SEP> und
<tb>  längere <SEP> Zeit <SEP> am <SEP> Rückfluss <SEP> gekocht. <SEP> Man <SEP> kann
<tb>  so <SEP> das <SEP> N-Acety7.-5-keto-1,2,2',3,4,5-hexahydro  bernz(ed)indol <SEP> in <SEP> guter <SEP> Ausbeute <SEP> erhalten.
<tb>  



  Das <SEP> auf <SEP> diese <SEP> Weise <SEP> hergestellte, <SEP> bisher
<tb>  unbekannte <SEP> 1\T-Acetyl-5-keto-1,2,2',3,4,5-hexa  hydro=benz(cd)indol <SEP> kristo!Ihsiert <SEP> aus <SEP> Essig  ester <SEP> in <SEP> Nadeln <SEP> vom <SEP> Schmielzpunkt <SEP> 175 <SEP> bis
<tb>  177 C. <SEP> Es <SEP> soll <SEP> als <SEP> Zwischenprodukt <SEP> verwen  det <SEP> werden..
<tb>  



  <I>Beispiel:</I>
<tb>  5,1 <SEP> g <SEP> ss-[1-Acety'1-4-car'box.--2,3-diihydro  indolyl(3) <SEP> ]-propionsäure <SEP> und <SEP> 0,51 <SEP> .g <SEP> frisch            pulverisiertes        Kaliumcyanid    löste man     =n     <B>250</B>     em3        friAch        destilliertem        Acetanhydrid    und  kochte die Lösung über Nacht am     Rückfluss.     Die braune Lösung verdampfte man im Va  kuum     zur    Trockne, löste den Rückstand in  Chloroform, schüttelte mit.

       Natriumhydrogeii-          carbonatlösung,    trocknete die Chloroform  lösung über Natriumsulfat und     verdampfte     zur Trockne.     Der        Rückstand        lieferte    aus  Essigester 2,93     g        kristallisierte,        N-Iicetyl-5-          'keto-1,2,2',3,4,5-hexahydro-beniz(cd)indo@l    vom       'Schmelzpunkt    175 bis 177 C,     entsprechend          einer        Ausbeute        von        74%.     



  Für die Analyse     wurde    eine Probe der  Substanz aus     Essigester        iunkristallisiert,    wo  durch sich der !Schmelzpunkt nicht mehr ver  änderte.  
EMI0001.0042     
  
    C13HIsO2N <SEP> (21'5,24'3) <SEP> Ber. <SEP> <B>072,54 <SEP> H6,09</B> <SEP> N <SEP> $,51%
<tb>  Gef. <SEP> 72,54 <SEP> 5,93 <SEP> 6,441/o            Keller-Reaktion    negativ,



      Process for making an indole series ketone.
EMI0001.0006
  
    <SEP> was found <SEP>, <SEP> that <SEP> one <SEP> to <SEP> N <SEP> Acetyl aketo-1,2,2 ', 3,4,5-hexahydro-benz (od ), indo'1 <SEP> ge lang4 <SEP> if <SEP> man <SEP> on <SEP> ss- [1-acetyl-4-carboxy 2,3-d-ihydro-indolyl <SEP> (3) <SEP>] <SEP> propionic acid <SEP> allows a <SEP> Cy <SEP> cloning agent to act using a catalyst.

   The following scheme illustrates the reaction:
EMI0001.0012
  
EMI0001.0013
  
    For the <SEP> execution <SEP> of the <SEP> according to the invention
<tb> Method <SEP> becomes <SEP> for <SEP> Example <SEP> ss <SEP> [1-Acetyl 4-carboxy <SEP> - <SEP> 2,3 <SEP> - <SEP> dihydro <SEP > - <SEP> indolyl <SEP> (3) <SEP>] <SEP> -propionic acid <SEP> and <SEP> potassium cyanide <SEP> (catalyst) <SEP> in
<tb> Acetic anhydride <SEP> (cyclizing agent) <SEP> dissolved <SEP> and
<tb> longer <SEP> time <SEP> on <SEP> reflux <SEP> boiled. <SEP> You can <SEP>
<tb> so <SEP> the <SEP> N-Acety7.-5-keto-1,2,2 ', 3,4,5-hexahydro bernz (ed) indole <SEP> in <SEP> good <SEP> Yield <SEP> obtained.
<tb>



  The <SEP> <SEP> produced this <SEP> way <SEP>, <SEP> so far
<tb> unknown <SEP> 1 \ T-acetyl-5-keto-1,2,2 ', 3,4,5-hexa hydro = benz (cd) indole <SEP> crystallized <SEP> from <SEP > Essig ester <SEP> in <SEP> needles <SEP> from <SEP> melting point <SEP> 175 <SEP> to
<tb> 177 C. <SEP> <SEP> should <SEP> be used as <SEP> intermediate product <SEP> <SEP> ..
<tb>



  <I> Example: </I>
<tb> 5.1 <SEP> g <SEP> ss- [1-Acety'1-4-car'box .-- 2,3-diihydro indolyl (3) <SEP>] -propionic acid <SEP> and < SEP> 0.51 <SEP> .g <SEP> freshly powdered potassium cyanide was dissolved = n <B> 250 </B> em3 of freshly distilled acetic anhydride and the solution was refluxed overnight. The brown solution was evaporated to dryness in a vacuum, the residue was dissolved in chloroform, and shaken.

       Sodium hydrogen carbonate solution, the chloroform solution dried over sodium sulfate and evaporated to dryness. The residue yielded 2.93 g of crystallized, N-licetyl-5- 'keto-1,2,2', 3,4,5-hexahydrobeniz (cd) indo @ l with a melting point of 175 to 177 ° C from ethyl acetate, corresponding to a yield of 74%.



  For the analysis, a sample of the substance was crystallized from ethyl acetate, where the melting point no longer changed.
EMI0001.0042
  
    C13HIsO2N <SEP> (21'5,24'3) <SEP> calc. <SEP> <B> 072.54 <SEP> H6.09 </B> <SEP> N <SEP> $, 51%
<tb> Found <SEP> 72.54 <SEP> 5.93 <SEP> 6.441 / o Keller reaction negative,

Claims (1)

PATEN TANSPRUCH Verfahren zur Herstellung von N-Aeetyl- 5.,keto -1,2,2',3,4; PATENT CLAIM Process for the preparation of N-acetyl-5., keto -1,2,2 ', 3,4; 5 - hexahydro - benz(cd) indol, dadurch gekennzeichnet, dass man auf ss-[1- Acetyl-4-carboxy 2,3-dihydro -indoldyl (3) ] -pro pionsäure ein Cyclisierungsmittel unter Ver- wendung eines Katalysators einwirken lässt. 5-hexahydro-benz (cd) indole, characterized in that a cyclizing agent is allowed to act on ss- [1-acetyl-4-carboxy 2,3-dihydro-indoldyl (3)] propionic acid using a catalyst . Die neue Verbindung besitzt die Brutto- formel Ci3Hi302N und, schmilzt bei 175 bis 177 C. geller Reaktion negativ. The new compound has the gross formula Ci3Hi302N and, melts at 175 to 177 C. Geller reaction negative. UNTERANSPRUCH Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass als Cyclisierungsmittel Acetanhydrid und als Katalysator Kalium- cyanid verwendet wird. SUBSTANTIAL CLAIM Process according to claim, characterized in that acetic anhydride is used as the cyclizing agent and potassium cyanide is used as the catalyst.
CH302151D 1951-11-30 1951-11-30 Process for making an indole series ketone. CH302151A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH302151T 1951-11-30

Publications (1)

Publication Number Publication Date
CH302151A true CH302151A (en) 1954-10-15

Family

ID=4491274

Family Applications (1)

Application Number Title Priority Date Filing Date
CH302151D CH302151A (en) 1951-11-30 1951-11-30 Process for making an indole series ketone.

Country Status (1)

Country Link
CH (1) CH302151A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2809974A (en) * 1954-11-12 1957-10-15 Lilly Co Eli Substituted-benz [cd] indoles and the preparation thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2809974A (en) * 1954-11-12 1957-10-15 Lilly Co Eli Substituted-benz [cd] indoles and the preparation thereof

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