GB761796A - New quinoline derivatives - Google Patents

New quinoline derivatives

Info

Publication number
GB761796A
GB761796A GB694654A GB694654A GB761796A GB 761796 A GB761796 A GB 761796A GB 694654 A GB694654 A GB 694654A GB 694654 A GB694654 A GB 694654A GB 761796 A GB761796 A GB 761796A
Authority
GB
United Kingdom
Prior art keywords
methylquinolyl
diamino
free base
amine
phenol
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
GB694654A
Inventor
Herbert Clare Carrington
Edwin Harry Paterson Young
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB694654A priority Critical patent/GB761796A/en
Publication of GB761796A publication Critical patent/GB761796A/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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4

Landscapes

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

Abstract

The invention comprises quinoline derivatives of the general formula <FORM:0761796/IV(b)/1> wherein X is -NH-, -O-, -S- or -CH2-, R and R1 are hydrogen or alkyl and R11 is alkyl and their preparation by heating the corresponding bis - (4 - halogenoquinoline) compounds with an amine HNRR1. The reaction may be conducted between 100 DEG and 200 DEG C., conveniently in the presence of a solvent such as phenol, and in some cases conveniently under increased pressure. In examples: (1) ammonia is blown into a melt of phenol and acetamide and 4 : 41 - dichloro - 6 : 61 - di (2 - methylquinolyl) amine is added. The product is isolated as 4 : 41-diamino-6 : 61-di-(2-methylquinolyl) amine dihydrochloride from which the free base is then liberated; (2) 4 : 41-di(methylamino) - 6 : 61 - di - (2 - methylquinolyl) amine dihydrochloride and the corresponding free base are obtained from the appropriate di-chloro compound and methylamine hydrochloride in a melt of phenol and caustic potash as solvent; (3) 4 : 41 - diamino - 6 : 61 - di - (2 - methylquinolyl) ether dihydrochloride and the corresponding free base are obtained by the method of Example (1); (4) 4 : 41-diamino-6 : 61-di-(2-methylquinolyl) methane is similarly prepared; (5) 4 : 41 - diamino - 6 : 61 - di - (2 - methylquinolyl) sulphide is similarly prepared; (6) 4 : 41 - bis - (dimethylamino)-6 : 61 - di(2 - methylquinolyl) amine dihydrochloride and the corresponding free base are prepared by the method of Example (2). Starting materials. The bis-(4-halogenoquinoline) compounds may be prepared by the action of, for example, phosphorus oxychloride on the corresponding hydroxy compounds which themselves may be obtained by ring closure by heat of the condensation product of, for example, an acetoacetic ester with a compound <FORM:0761796/IV(b)/2> Specification 761,797 is referred to.
GB694654A 1954-03-10 1954-03-10 New quinoline derivatives Expired GB761796A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB694654A GB761796A (en) 1954-03-10 1954-03-10 New quinoline derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB694654A GB761796A (en) 1954-03-10 1954-03-10 New quinoline derivatives

Publications (1)

Publication Number Publication Date
GB761796A true GB761796A (en) 1956-11-21

Family

ID=9823745

Family Applications (1)

Application Number Title Priority Date Filing Date
GB694654A Expired GB761796A (en) 1954-03-10 1954-03-10 New quinoline derivatives

Country Status (1)

Country Link
GB (1) GB761796A (en)

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