CH122466A - Process for the preparation of 1-phenyl-2-methyl-3,4-cyclotrimethylene-5-pyrazolone. - Google Patents

Process for the preparation of 1-phenyl-2-methyl-3,4-cyclotrimethylene-5-pyrazolone.

Info

Publication number
CH122466A
CH122466A CH122466DA CH122466A CH 122466 A CH122466 A CH 122466A CH 122466D A CH122466D A CH 122466DA CH 122466 A CH122466 A CH 122466A
Authority
CH
Switzerland
Prior art keywords
phenyl
pyrazolone
methyl
cyclotrimethylene
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH122466A publication Critical patent/CH122466A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

  

      Verfahren    zur Darstellung von     1-Phenyl-2-methyl-3,4-eyclotrimethylen-5-pyrazolon.       Gegenstand der . vorliegenden Erfindung  ist ein Verfahren zur Darstellung von 1-Phe       nyl-2-methyl-3,4-cyclotrimethylen-5-pyrazo-          lon,    welches dadurch     gekennzeichnet    ist, dass  man     Cyclopentanonkarbonsäureäthylester    auf       a-Phenyl-ss-methylhydrazin    bei     Gegenwart     von     Kondensationsmitteln        einwirken    lässt.  



  Durch die deutsche Patentschrift Nr. 40377  ist ein Verfahren zur Herstellung von     1-Phe-          nyl-2,3-dimethyl-5-pyrazolon        bekannt    gewor  den, nach welchem man     Acetessigester    mit  symmetrischem     Methylphenylhydrazin    kon  densiert.

   Erhitzt man nach Vorschrift des       erwähnten    Patentes     Cyclopentanonkarbon-          säureäthylester        mit        a-Phenyl-ss-methylhydra-          zin,    so erhält man das     ss-Cyclopentenkarbon-          säurederivat    des     a-Phenyl-ss-methylhydrazins,     aber kein     Pyrazolonderivat.    Auch eine Steige  rung der Temperatur führt nicht zum Ring  schluss. Es bilden sich nur Zersetzungspro  dukte.

   Daher war es nicht zu     erwarten,    dass  der     Ringschluss    sich leicht vollzieht, wenn       Kondensationsmittel    zur Anwendung gelan  gen. Als Kondensationsmittel können Na-         triumäthylat,        Natriumamid,        Natriummethy-          lat    usw. verwendet     werden.     



  Das     1-Phenyl-2-methyl-3,4-cyclotrime-          thylen-5-pyrazolon    bildet farblose prisma  tische     Kristalle,    die bei 128   schmelzen. Es  löst sich in Wasser und Äther schwer, in  Alkohol, Benzol und in Säuren leicht und soll  in der Therapie     Verwendung    finden.    <I>Beispiel:</I>  156 Teile     Cyclopentanonkarbonsäure-          äthylester        (Kp"108     ) und 122 Teile     a-Phe-          nyl-ss-methylhydrazin        werden    gemischt, wo  bei sie unter Ausscheidung von Wasser mit  einander reagieren.

   Das Reaktionsprodukt  wird sorgfältig im Vakuum getrocknet und  mit einer aus 46 Teilen Natrium in 540 Tei  len absolutem Alkohol hergestellten Natrium  äthylatlösung versetzt. Der Alkohol wird im  Vakuum     abdestilliert    und der Rückstand' zwei  Stunden auf 140' erhitzt.

   Nach dem Ab  kühlen wird die Reaktionsmasse in 10%iger  Salzsäure gelöst, vom wenigen ungelösten 01  abgetrennt und das 1-Phenyl-2-methyl-3,4-           eyclotrimethylen-5-pyrazolon    durch die     be-          v=ehnete        AZenge        Natriumhydroxydlösung        aus-          "C-fällt.    Es bildet nach dem     Umkristallisieren          üns    Nasser farblose prismatische Kristalle,  die bei<B>128</B>   schmelzen.



      Process for the preparation of 1-phenyl-2-methyl-3,4-eyclotrimethylene-5-pyrazolone. Subject of. The present invention is a process for the preparation of 1-phenyl-2-methyl-3,4-cyclotrimethylene-5-pyrazolone, which is characterized in that ethyl cyclopentanone carboxylate is acted on a-phenyl-ß-methylhydrazine in the presence of condensing agents leaves.



  Through the German patent specification No. 40377 a process for the preparation of 1-phenyl-2,3-dimethyl-5-pyrazolone has become known, according to which acetoacetic ester condenses with symmetrical methylphenylhydrazine.

   If ethyl cyclopentanone carbonate is heated with α-phenyl-β-methylhydrazine according to the instructions in the patent mentioned, the α-phenyl-β-methylhydrazine derivative is obtained, but no pyrazolone derivative. An increase in temperature does not lead to ring closure either. Only decomposition products are formed.

   It was therefore not to be expected that the ring closure would take place easily if condensation agents were used. Sodium ethylate, sodium amide, sodium methylate, etc. can be used as condensation agents.



  The 1-phenyl-2-methyl-3,4-cyclotrimethylene-5-pyrazolone forms colorless prismatic crystals that melt at 128. It dissolves with difficulty in water and ether, easily in alcohol, benzene and acids and is said to be used in therapy. <I> Example: </I> 156 parts of ethyl cyclopentanone carboxylate (bp "108) and 122 parts of a-phenyl-ss-methylhydrazine are mixed, where they react with each other with the elimination of water.

   The reaction product is carefully dried in vacuo and a sodium ethylate solution prepared from 46 parts of sodium in 540 parts of absolute alcohol is added. The alcohol is distilled off in vacuo and the residue is heated to 140 for two hours.

   After cooling, the reaction mass is dissolved in 10% hydrochloric acid, separated from the little undissolved oil, and the 1-phenyl-2-methyl-3,4-eyclotrimethylene-5-pyrazolone is eliminated with the aforementioned amount of sodium hydroxide solution. C. After recrystallization, it forms colorless prismatic crystals in water, which melt at <B> 128 </B>.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 1-Phenyl- --methyl -3,4- cyclotrimethylen -5- pyrazolon, dadurch gekennzeichnet, dass man Cyclopen- tanonl@arbonsäureäthylester auf a.-Phenyl-ss- methylhydrazin in Gegenwart von Konden- sationsmitteln einwirken lässt. PATENT CLAIM: Process for the preparation of 1-phenyl-methyl -3,4-cyclotrimethylene -5-pyrazolone, characterized in that ethyl cyclopentanone-ethyl ester acts on α-phenyl-ss-methylhydrazine in the presence of condensation agents leaves. Das 1-Phenyl-3-methyl-3,4-cyclotrimethy- len-5-pyrazolon bildet farblose prismatische Kristalle, die bei 138 schmelzen. Es löst sich in Wasser und Äther schwer, in Alkohol, Penzol und in Säuren leicht und soll in der Therapie Venvendung finden. The 1-phenyl-3-methyl-3,4-cyclotrimethylene-5-pyrazolone forms colorless prismatic crystals that melt at 138. It dissolves with difficulty in water and ether, easily in alcohol, penzene and acids and is intended to be used in therapy.
CH122466D 1926-05-12 1926-05-12 Process for the preparation of 1-phenyl-2-methyl-3,4-cyclotrimethylene-5-pyrazolone. CH122466A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH122466T 1926-05-12

Publications (1)

Publication Number Publication Date
CH122466A true CH122466A (en) 1927-09-16

Family

ID=4381240

Family Applications (1)

Application Number Title Priority Date Filing Date
CH122466D CH122466A (en) 1926-05-12 1926-05-12 Process for the preparation of 1-phenyl-2-methyl-3,4-cyclotrimethylene-5-pyrazolone.

Country Status (1)

Country Link
CH (1) CH122466A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2731473A (en) * 1956-01-17 New pyrazolone derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2731473A (en) * 1956-01-17 New pyrazolone derivatives

Similar Documents

Publication Publication Date Title
CH122466A (en) Process for the preparation of 1-phenyl-2-methyl-3,4-cyclotrimethylene-5-pyrazolone.
AT165070B (en) Process for the preparation of the new 5,6,7,8-tetrahydroisoquinoline
CH240363A (en) Process for the preparation of N- (y, y-diphenyl-allyl) -piperidine.
DE587428C (en) Process for the preparation of 1, 5, 5- and 1, 3, 5, 5-substituted barbituric acids
DE729850C (en) Process for the preparation of 2,4-dioxooxazolidines substituted in the 5-position
DE921265C (en) Process for the preparation of aryl-substituted pyrazoline compounds
DE503031C (en) Process for the preparation of the N-oxyethyl derivatives of core substitution products of -amino-1-oxybenzene
CH218517A (en) Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-isopropyl-ketone.
DE479354C (en) Process for the preparation of 1-amino-3-dialkylamino-2-propanols
AT160752B (en) Method for the preparation of pregnen- (4) -dione- (3.20).
DE512233C (en) Process for the preparation of 1-aminocarbazole and its derivatives
AT206899B (en) Process for the preparation of new, substituted 3,5-dioxo-tetrahydro-1,2,6-thiadiazine-1,1-dioxyden
DE639125C (en) Process for the preparation of condensation products of phloroglucinol
AT115634B (en) Process for the preparation of 1-pyridyl-2,3-dimethyl-5-pyrazolone derivatives.
AT129783B (en) Process for the preparation of 2-oxymethylbenzimidazolaric acids.
CH199906A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH160940A (en) Process for the preparation of a 4-oxypyridine derivative.
CH211294A (en) Process for the production of a condensation product.
CH159081A (en) Process for the preparation of 4-benzyl-6-methyl-3-keto-3,4-dihydro-1,4-benzoxazine.
CH128225A (en) Process for the preparation of 6-methoxy-8-aminoquinoline.
CH134220A (en) Process for the production of choline monoborate from choline and boric acid.
CH114009A (en) Method for the preparation of benzylresorcinol.
DE1493434A1 (en) Process for the preparation of 2- (N-acyloxy-N-acylamido) acetic acid derivatives
CH222484A (en) Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-propyl-ketone.
CH168011A (en) Process for the preparation of 1-phenyl-3-methyl-4-cyclohexylpyrazolone.