GB1122435A - Process for the preparation of derivatives of quinoline 3-carboxylates - Google Patents

Process for the preparation of derivatives of quinoline 3-carboxylates

Info

Publication number
GB1122435A
GB1122435A GB7131566A GB7131566A GB1122435A GB 1122435 A GB1122435 A GB 1122435A GB 7131566 A GB7131566 A GB 7131566A GB 7131566 A GB7131566 A GB 7131566A GB 1122435 A GB1122435 A GB 1122435A
Authority
GB
United Kingdom
Prior art keywords
quinoline
alkyl
anil
halogen
formula
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
GB7131566A
Inventor
Raymond Alexander Bowie
Mervyn Stuart Grant
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
Publication of GB1122435A publication Critical patent/GB1122435A/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
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

Quinoline derivatives of the formula <FORM:1122435/C2/1> where R1 represents a C12-C14- alkyl group or an aralkyl group optionally substituted by halogen or alkyl or nitro radicals, R2 represents an alkyl group and the benzene moiety of the quinoline nucleus may be substituted by halogen or alkyl, alkenyl or alkoxy groups, are prepared by reacting an anil of the formula <FORM:1122435/C2/2> where the benzene nucleus may be optionally substituted as above, with a phosphorus oxyhalide followed, if necessary, by hydrolysis of the 4-halogeno-quinoline when formed. If approximately equimolar amounts of the anil and the phosphorus oxychloride are used, the reaction yields the 4-hydroxy-quinoline derivative. An excess of phosphorus oxyhalide yields the 4-halogeno derivative which may be hydrolysed under acidic or basic conditions, e.g. using an acetic acid/sodium acetate mixture, The cyclisation reaction is preferably effected by heating the reactants in an inert diluent, e.g. toluene.
GB7131566A 1966-04-20 1966-04-20 Process for the preparation of derivatives of quinoline 3-carboxylates Expired GB1122435A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1731566 1966-04-20
GB1731567 1967-03-14

Publications (1)

Publication Number Publication Date
GB1122435A true GB1122435A (en) 1968-08-07

Family

ID=26252606

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7131566A Expired GB1122435A (en) 1966-04-20 1966-04-20 Process for the preparation of derivatives of quinoline 3-carboxylates

Country Status (8)

Country Link
BE (1) BE697312A (en)
CH (1) CH553783A (en)
CS (1) CS160086B2 (en)
DK (1) DK117768B (en)
ES (1) ES339542A2 (en)
GB (1) GB1122435A (en)
NL (1) NL6705539A (en)
SE (1) SE369901B (en)

Cited By (1)

* 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

Cited By (1)

* 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

Also Published As

Publication number Publication date
CS160086B2 (en) 1975-02-28
NL6705539A (en) 1967-10-23
CH553783A (en) 1974-09-13
BE697312A (en) 1967-10-20
DE1695275B1 (en) 1972-08-31
ES339542A2 (en) 1968-05-16
SE369901B (en) 1974-09-23
DK117768B (en) 1970-06-01

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