DE423026C - Process for the preparation of a Bz-tetrahydrooxyquinoline - Google Patents

Process for the preparation of a Bz-tetrahydrooxyquinoline

Info

Publication number
DE423026C
DE423026C DER59139D DER0059139D DE423026C DE 423026 C DE423026 C DE 423026C DE R59139 D DER59139 D DE R59139D DE R0059139 D DER0059139 D DE R0059139D DE 423026 C DE423026 C DE 423026C
Authority
DE
Germany
Prior art keywords
tetrahydrooxyquinoline
preparation
compound
alcohol
oxyquinoline
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
DER59139D
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.)
Honeywell Riedel de Haen AG
Original Assignee
JD Riedel 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 JD Riedel AG filed Critical JD Riedel AG
Priority to DER59139D priority Critical patent/DE423026C/en
Application granted granted Critical
Publication of DE423026C publication Critical patent/DE423026C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Darstellung eines Bz-Tetrahydrooxychinolins. Es ist* bekannt, daß der Pyridinkern des Chinolins leichter hydrierbar ist als der Benzolkern. v. Braun (vgl. Ber. 55 [1922] S. 3779 bis 3792) hat ferner gezeigt,, daß auch solche Derivate des Chinolins, welche im Benzolkern durch Alkyl- substituiert sind, bei der Hydrierung ausschließlich Py-Tetrahydro-Verbindungen ergeben. Es wurde nun ganz im Gegensatz hierzu gefunden, daß 2, 4-Dimethyl-6-oxychinolin bei der katalytischen Hydrierung in Gegenwart von Nickelkatalysator lediglich die Bz-Tetrahydro-Verbindung liefert. Dieser Reaktionsverlauf erscheint um so überraschender, als im Pyridinkern der erwähnten Verbindung zwei Alkylgruppen enthalten sind.Process for the preparation of a Bz-tetrahydrooxyquinoline. * It is known that the pyridine ring of the quinoline is lighter hydrogenatable than the benzene nucleus. v. Braun (cf. Ber. 55 [1922] pp. 3779 to 3792) has also shown that those derivatives of quinoline which are substituted by alkyl in the benzene nucleus also give exclusively Py-tetrahydro compounds on hydrogenation. In complete contrast to this, it has now been found that 2,4-dimethyl-6-oxyquinoline only gives the Bz-tetrahydro compound in the catalytic hydrogenation in the presence of a nickel catalyst. This course of the reaction appears all the more surprising since the pyridine nucleus of the compound mentioned contains two alkyl groups.

Die neue Verbindung soll zur Herstellung therapeutischer Präparate verwendet werden. So liefert sie z. B. bei der Benzoylierung einaußerordentlich wirksames Anästhetikum.The new compound is said to be used to manufacture therapeutic preparations be used. So she delivers z. B. extraordinary in benzoylation effective anesthetic.

Beispiel. Durch Erwärmen von Phenetidin mit Acetylaceton und Behandlung des erhaltenen Phenetidids mit konzentrierter Schwefelsäure gelangt man zu dem bekannten 2, ,1-Dimethyl-6-oxychinolin. Läßt man au, dieses, nachdem man es vorher zweckm.äPi,; in Dekahydronaphthalin gelöst hat, bei i 8o bis i 9o° in Gegenwart eines nickelhaltigen Katalysators Wasserstoff unter Druck einwirken, so erhält man nach dem Verdünnen-mit Alkohol und Abfiltrieren vom Katalysator eine Lösung, die nach dem Abdestillieren des Alkohols und Dekahydronaphthalins eine in Alkali unlösliche Kristallnasse hinterläßt. Sie schmilzt nach dem Umkristallisieren aus Alkohol bei 162" und zeigt die empirische Zusammensetzung C11 Hl.; NO. Die neue Base, welche mit einer Ausbeute von etwa 98 Prozent gewonnen wird, siedet bei i 8 i bis 183° (unter i 5 mm Druck) und erstarrt restlos beim Erkalten. Mit salpetriger Säure tritt keine Reaktion ein. Das Chlorhydrat schmitzt bei 134.°, das Pikrat bei 15o° und das jodmethylat bei i -Io". Die Analyse des Jodmethylats ergibt 39.9= Prozent Jod entsprechend der Formel C"H1sONJ. Erwärmt man die Base in Chloroformlösu:ng eine halbe Stunde mit Benzoylchlorid und setzt Äther zu, so fällt das Chlorhydrat der O-Benzoyl-Verbindung als weißes Kristallpulver vom Schmelzpunkt i99 bis 2oo'c aus.Example. By heating phenetidine with acetylacetone and treating of the phenetidide obtained with concentrated sulfuric acid leads to the known 2,, 1-Dimethyl-6-oxyquinoline. If one leaves this out after one has previously expedited it; has dissolved in decahydronaphthalene at i 8o to i 9o ° in the presence of a nickel-containing one If the catalyst acts under pressure, hydrogen is obtained after dilution with Alcohol and filtering off the catalyst a solution that after distilling off of the alcohol and decahydronaphthalene leaves a crystalline liquid insoluble in alkali. It melts at 162 "after recrystallization from alcohol and shows the empirical Composition C11 Hl .; NO. The new base, which with a yield of about 98 Percent is obtained, boils at i 8 i to 183 ° (under i 5 mm pressure) and solidifies completely when cooling down. There is no reaction with nitrous acid. The hydrochloride Schmitz at 134 °, the picrate at 150 ° and the iodomethylate at i -Io ". The analysis of the iodine methylate gives 39.9 = percent iodine according to the formula C "H1sONJ. Heated the base is dissolved in chloroform solution with benzoyl chloride for half an hour and is set If ether is added, the hydrochloride of the O-benzoyl compound falls as a white crystal powder from melting point 199 to 2oo'c.

Claims (1)

PATLN'T-ANSPRUCH: Verfahren zur Darstellung eines Bz-Tetrahydrooxychinolins, dadurch gekennzeichnet, daß man 2, ,1-Dimethyl-6-oxychinolin in Gegenwart eines nickelhaltigen Katalysators mit molekularem Wasserstoff behandelt.PATLN'T CLAIM: Process for the preparation of a Bz-tetrahydrooxyquinoline, characterized in that 2,, 1-dimethyl-6-oxyquinoline in the presence of a nickel-containing catalyst treated with molecular hydrogen.
DER59139D 1923-08-10 1923-08-10 Process for the preparation of a Bz-tetrahydrooxyquinoline Expired DE423026C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DER59139D DE423026C (en) 1923-08-10 1923-08-10 Process for the preparation of a Bz-tetrahydrooxyquinoline

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER59139D DE423026C (en) 1923-08-10 1923-08-10 Process for the preparation of a Bz-tetrahydrooxyquinoline

Publications (1)

Publication Number Publication Date
DE423026C true DE423026C (en) 1925-12-18

Family

ID=7410991

Family Applications (1)

Application Number Title Priority Date Filing Date
DER59139D Expired DE423026C (en) 1923-08-10 1923-08-10 Process for the preparation of a Bz-tetrahydrooxyquinoline

Country Status (1)

Country Link
DE (1) DE423026C (en)

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