GB1122323A - Quinoline derivatives - Google Patents

Quinoline derivatives

Info

Publication number
GB1122323A
GB1122323A GB3497866A GB3497866A GB1122323A GB 1122323 A GB1122323 A GB 1122323A GB 3497866 A GB3497866 A GB 3497866A GB 3497866 A GB3497866 A GB 3497866A GB 1122323 A GB1122323 A GB 1122323A
Authority
GB
United Kingdom
Prior art keywords
stands
alkyl
radical
formula
anil
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
GB3497866A
Inventor
Mervyn Stuart Grant
William Glynne Moss Jones
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 GB3497866A priority Critical patent/GB1122323A/en
Publication of GB1122323A publication Critical patent/GB1122323A/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
    • C07D215/48—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
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Quinoline Compounds (AREA)

Abstract

Novel quinoline derivatives of the formula <FORM:1122323/C2/1> wherein R1 stands for alkyl or alkenyl, R2 stands for an alkyl radical of at least 2 carbon atoms or for an aralkyl radical, and R3 stands for hydrogen or an alkyl, alkoxy or alkylthio radical, are obtained by cyclizing an anil of the formula <FORM:1122323/C2/2> wherein R1, R2 and R3 are as defined above Cyclization may be effected by heating above 200 DEG C. or by interaction of the anil with phosphorus oxyhalide if desired followed by hydrolysis of the 4-substituted quinoline derivative so formed. The free acid may be converted to its ester by standard esterification procedures. The starting anil may be obtained by condensing an aniline derivative of the formula <FORM:1122323/C2/3> with a compound of the formula R4O.CH = C(COOR1)2 3-Benzylthio-4-ethylacetanilide is obtained by heating 5-acetylamino-2-ethylthiophenol with benzyl chloride. 5 - Acetylamino - 2 - ethyl - thiophenol is obtained by acetylating 5 - amino - 2 - ethylthiophenol. 3 - Benzylthioaniline is obtained by reducing 3 - benzylthionitrobenzene which is obtained by treating 3 - nitrothiophenol with benzyl chloride. 3,4 - Di - n - butylthioaniline is obtained by reacting 3,4 - dibromonitrobenzene with cuprous n - butylimercaptide to form 3,4 - di - n - butylthionitrobenzene which is reduced with Na2S. 3 - n - Octylthio - 4 - n - propylthioaniline is obtained by treating 3,4-dibromonitrobenzene with Na2S to form 3-bromo-4-mercaptonitrobenzene, treating the latter with iodopropane to form 3 - bromo - 4 - n - propylthionitrobenzene and reacting the latter with cuprous - n - octylmercaptide. 4 - Isobutoxy - 3 - isobutylthioaniline is obtained by heating 4 - hydroxy - 3 - mercaptoacetanilide with isobutyl iodide to form 4 - isobutoxy - 3 - isobutylthioacetanilide and hydrolysing the latter with NaOH.ALSO:Anti-coccidial compositions comprise one or more quinoline derivatives of the formula: <FORM:1122323/A5-A6/1> wherein R1 stands for an alkyl or alkenyl radical, R2 stands for an alkyl radical of at least 2 carbon atoms or for an aralkyl radical, and R3 stands for hydrogen or an alkyl, alkoxy or alkylthio radical, together with a non-toxic diluent or p carrier e.g. kaolin, talc, calcium carbonate, fullers earth, attapulgus clay, ground oyster shells, whole ground corn, corn distillers dry grain, wheat shorts or corn cob meal. Additionally there may be present one or more known coccidiostats, anthelmintics, growth promoters, anti-bacterials and tranquillizers.
GB3497866A 1966-08-04 1966-08-04 Quinoline derivatives Expired GB1122323A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3497866A GB1122323A (en) 1966-08-04 1966-08-04 Quinoline derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3497866A GB1122323A (en) 1966-08-04 1966-08-04 Quinoline derivatives

Publications (1)

Publication Number Publication Date
GB1122323A true GB1122323A (en) 1968-08-07

Family

ID=10372350

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3497866A Expired GB1122323A (en) 1966-08-04 1966-08-04 Quinoline derivatives

Country Status (1)

Country Link
GB (1) GB1122323A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3472859A (en) * 1966-11-01 1969-10-14 Sterling Drug Inc 1-alkyl-1,4-dihydro-4-oxo-3 quinoline-carboxylic acids and esters
FR2002888A1 (en) * 1968-02-29 1969-10-31 Warner Lambert Pharmaceutical
EP0339406A1 (en) * 1988-04-19 1989-11-02 Hokuriku Pharmaceutical Co.,Ltd Quinoline-3-carboxylic acid derivatives, process for preparing the same, and composition exhibiting excellent antibacterial effect containing the same
FR2677649A1 (en) * 1991-06-13 1992-12-18 Oreal SULFUR METAAMINOPHENOLS, THEIR APPLICATION FOR CAPILLARY DYE.

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3472859A (en) * 1966-11-01 1969-10-14 Sterling Drug Inc 1-alkyl-1,4-dihydro-4-oxo-3 quinoline-carboxylic acids and esters
FR2002888A1 (en) * 1968-02-29 1969-10-31 Warner Lambert Pharmaceutical
EP0339406A1 (en) * 1988-04-19 1989-11-02 Hokuriku Pharmaceutical Co.,Ltd Quinoline-3-carboxylic acid derivatives, process for preparing the same, and composition exhibiting excellent antibacterial effect containing the same
FR2677649A1 (en) * 1991-06-13 1992-12-18 Oreal SULFUR METAAMINOPHENOLS, THEIR APPLICATION FOR CAPILLARY DYE.
WO1992022525A1 (en) * 1991-06-13 1992-12-23 L'oreal Use of suplhurous metaaminophenols for dying keratinic fibres, tinctorial compositions and novel compounds

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