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DE1170955B - Process for the preparation of 2-methylmercapto-3-cyano-4-chloroquinoline - Google Patents

Process for the preparation of 2-methylmercapto-3-cyano-4-chloroquinoline

Info

Publication number
DE1170955B
DE1170955B DEF37889A DEF0037889A DE1170955B DE 1170955 B DE1170955 B DE 1170955B DE F37889 A DEF37889 A DE F37889A DE F0037889 A DEF0037889 A DE F0037889A DE 1170955 B DE1170955 B DE 1170955B
Authority
DE
Germany
Prior art keywords
methylmercapto
cyano
heated
chloroquinoline
methyl ester
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.)
Pending
Application number
DEF37889A
Other languages
German (de)
Inventor
Dr Rudolf Gompper
Dr Werner Toepfl
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Priority to DEF37889A priority Critical patent/DE1170955B/en
Publication of DE1170955B publication Critical patent/DE1170955B/en
Pending 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3

Landscapes

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

Description

Verfahren zur Herstellung von 2-Methylmercapto-3-cyano4-chlorchinolin Es wurde ein Verfahren zur Herstellung von 2-Methylmercapto-3-cyano-4-chlorchinolin gefunden, bei dem man zunächst l-Cyano-2,2-bis-(methylmercapto)-arylsäuremethylester mit Anilin in Gegenwart von Athanol erhitzt, den so entstandenen 2- Methylmercapto -2- anilino - 1 - cyano - acrylsäuremethylester isoliert und mit überschüssigem Phosphoroxychlorid erhitzt.Process for the preparation of 2-methylmercapto-3-cyano4-chloroquinoline A process for the production of 2-methylmercapto-3-cyano-4-chloroquinoline has been established found, in which one initially l-cyano-2,2-bis (methylmercapto) -aryl acid methyl ester heated with aniline in the presence of ethanol, the resulting 2-methyl mercapto -2- anilino-1-cyano-acrylic acid methyl ester isolated and with excess Phosphorus oxychloride heated.

Die Verfahrenserzeugnisse sollen als Zwischenprodukte für weitere Synthesen, z. B. für die Herstellung von Farbstoffen oder Heilmitteln dienen. The process products are intended as intermediate products for further Syntheses, e.g. B. serve for the production of dyes or medicines.

Beispiel 4,1 g 1- Cyano - 2,2-bis - (methylmercapto) - acrylsäuremethylester und 9 ccm Anilin werden in 25 ccm Äthanol 1/2 Stunde unter Rückfluß zum Sieden erhitzt. Danach werden Lösungsmittel und überschüssiges Anilin im Vakuum abdestilliert, und der Rückstand wird mit Methanol angerieben. Fast farblose Kristallmasse (4,9 g). Aus Methanol umkristallisiert; Schmelzpunkt 79 bis 81°C. Farblose Nädelchen. Example 4.1 g of 1-cyano-2,2-bis (methylmercapto) -acrylic acid methyl ester and 9 cc of aniline are refluxed for 1/2 hour in 25 cc of ethanol. The solvent and excess aniline are then distilled off in vacuo, and the residue is rubbed with methanol. Almost colorless crystal mass (4.9 g). Recrystallized from methanol; Melting point 79 to 81 ° C. Colorless needles.

5,0 g des so hergestellten 2-Methylmercapto-2-anilino-1-cyano-acrylsäuremethylesters werden mit 5.0 g of the 2-methylmercapto-2-anilino-1-cyano-acrylic acid methyl ester prepared in this way are mixed with

Claims (1)

Patentanspruch: Verfahren zur Herstellung von 2-Methylmercapto-3-cyano-4-chlorchinolin, d a d u r c h gekennzeichnet, daß man zunächst 1 - Cyano - 2,2- bis - (methylmercapto) - acrylsäure-25 ccm rohem POCI3 1/2 Stunde unter Rückfluß zum Sieden erhitzt; die Lösung färbt sich dabei rotbraun.Claim: Process for the production of 2-methylmercapto-3-cyano-4-chloroquinoline, d a d u r c h that first 1 - cyano - 2,2- bis - (methylmercapto) - Acrylic acid-25 ccm of crude POCI3 heated to boiling under reflux for 1/2 hour; the The solution turns reddish brown. Nach dem Erkalten wird in 100 ccm Eiswasser eingerührt. Es scheidet sich ein Öl ab, das nach einiger Zeit kristallisiert. Umkristallisiert aus Methanol erhält man das 4-Chlor-2-methylmercapto-3-cyanochinolin, Schmelzpunkt 130 bis 133"C. Farblose Nädelchen. Ausbeute 1,4 g (300/0 der Theorie).After cooling, it is stirred into 100 cc of ice water. It part an oil that crystallizes after a while. Recrystallized from methanol 4-chloro-2-methylmercapto-3-cyanoquinoline, melting point 130 to 133 ° C., is obtained. Colorless needles. Yield 1.4 g (300/0 of theory). Die Umsetzung verläuft nach der Formel methylester mit Anilin in Gegenwart von Äthanol erhitzt, den so entstandenen 2-Methylmercapto-2 - anilino -1- cyano - acrylsäuremethylester isoliert und mit überschüssigem Phosphoroxychlorid erhitzt. The reaction proceeds according to the formula methyl ester with aniline in Heated in the presence of ethanol, the resulting 2-methylmercapto-2 - anilino -1- cyano - acrylic acid methyl ester isolated and with excess phosphorus oxychloride heated.
DEF37889A 1961-06-10 1961-06-10 Process for the preparation of 2-methylmercapto-3-cyano-4-chloroquinoline Pending DE1170955B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF37889A DE1170955B (en) 1961-06-10 1961-06-10 Process for the preparation of 2-methylmercapto-3-cyano-4-chloroquinoline

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF37889A DE1170955B (en) 1961-06-10 1961-06-10 Process for the preparation of 2-methylmercapto-3-cyano-4-chloroquinoline

Publications (1)

Publication Number Publication Date
DE1170955B true DE1170955B (en) 1964-05-27

Family

ID=7097104

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF37889A Pending DE1170955B (en) 1961-06-10 1961-06-10 Process for the preparation of 2-methylmercapto-3-cyano-4-chloroquinoline

Country Status (1)

Country Link
DE (1) DE1170955B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0459140A2 (en) * 1990-05-03 1991-12-04 BASF Aktiengesellschaft Cyanoquinolines as herbicides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0459140A2 (en) * 1990-05-03 1991-12-04 BASF Aktiengesellschaft Cyanoquinolines as herbicides
EP0459140A3 (en) * 1990-05-03 1992-05-20 Basf Aktiengesellschaft Cyanoquinolines as herbicides
US5565408A (en) * 1990-05-03 1996-10-15 Basf Aktiengesellschaft Cyanoquinoline compounds

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