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GB637863A - Improvements in or relating to process of preparing new quinoline antimalarial compounds and the compounds resulting therefrom - Google Patents

Improvements in or relating to process of preparing new quinoline antimalarial compounds and the compounds resulting therefrom

Info

Publication number
GB637863A
GB637863A GB4726/47A GB472647A GB637863A GB 637863 A GB637863 A GB 637863A GB 4726/47 A GB4726/47 A GB 4726/47A GB 472647 A GB472647 A GB 472647A GB 637863 A GB637863 A GB 637863A
Authority
GB
United Kingdom
Prior art keywords
prepared
general formula
reacting
alkoxypentane
halo
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
GB4726/47A
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.)
JOHN O NEILL VAN HOOK
Original Assignee
JOHN O NEILL VAN HOOK
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 JOHN O NEILL VAN HOOK filed Critical JOHN O NEILL VAN HOOK
Publication of GB637863A publication Critical patent/GB637863A/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
    • 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
    • C07D215/18—Halogen atoms or nitro radicals
    • 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
    • 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
    • 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
    • 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
    • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Substituted quinolines of the general formula <FORM:0637863/IV (b)/1> wherein R1 and R2 represent alkyl groups and R3 is hydrogen or an alkyl group, are prepared by reacting an 8-amino-6-alkoxy-quinoline with a 1-halo-5-alkylaminopentane hydrohalide of the general formula <FORM:0637863/IV (b)/2> wherein R1, R2 and R3 have the above significance and Ha represents a halogen, to obtain a salt of the desired quinoline and subsequently treating the reaction mixture with an alkali to liberate the desired free base. The substituted quinolines may be converted into their corresponding salts by the addition of mineral acids. In examples, 8-(51-isopropyl-aminopentylamino) - 6 - methoxyquinoline and its monophosphate salt, and 8-(51-tert.-butyl aminopentylamino) - 6 - methoxyquinoline are prepared. 1 - Halo - 5 - alkylaminopentane hydrohalides of the formula <FORM:0637863/IV (b)/3> , where Ha, R1, R2 and R3 have the above significance, are prepared by reacting the corresponding 5-alkylaminopentanol with a thionyl halide, or by reacting a 1-halo-5-alkoxypentane with an alkylamine of the general formula <FORM:0637863/IV (b)/4> , to form a 1-alkylamino-5-alkoxy-pentane which is then heated with a hydrohalide acid. In the examples, 1 - bromo - 5 - isopropylaminopentane hydrobromide, 1 - tert. - butylamino - 5 - chloropentane hydrochloride and 5-chloro-1-isopropylaminopentane hydrochloride are prepared. 1 - Alkylamino-5-alkoxypentanes of the general formula <FORM:0637863/IV (b)/5> , where R1, R2 and R3 have the above significance, are prepared by reacting the corresponding 1-halo-5-alkoxypentane with an alkylamine of the general formula <FORM:0637863/IV (b)/6> , or by reacting the desired 1-halo-5-alkoxypentane with potassium phthalimide to form the phthalimido derivative, hydrolysing to give 1-amino-5-alkoxypentane (which may also be obtained by reacting 1-bromo-5-methoxypentane with ammonia or with sodamide in liquid ammonia) and subsequently hydrogenating the 1-amino-5-alkoxypentane in the presence of an alkyl ketone and a hydrogenation catalyst. In an example, 1-isopropylamino-5-methoxypentane is prepared. 5 - Alkylamino - 1 - pentanol hydrohalide of the general formula <FORM:0637863/IV (b)/7> where Ha, R1, R2 and R3 have the above significance, are prepared by treating dihydropyran with hydrochloric acid and an alkylamine of the general formula <FORM:0637863/IV (b)/8> , hydrogenating the resulting mixture in the presence of a hydrogenation catalyst and then adding a hydrohalide acid. In examples, 5-isopropylamino-1-pentanol hydrochloride and 1-tert.-butylamino-5-pentanol hydrochloride are prepared. 1-Bromo-5-methoxypentane is prepared by reacting 1 : 5-dibromopentane and sodium methoxide. Some 1 : 5-dimethoxypentane is obtained.ALSO:An internal remedy comprises a mixture of quinine and a substituted quinoline of the general formula <FORM:0637863/VI/1> wherein R1 and R2 represent alkyl groups and R3 is hydrogen or an alkyl group, or a mineral acid salt thereof.
GB4726/47A 1946-02-19 1947-02-18 Improvements in or relating to process of preparing new quinoline antimalarial compounds and the compounds resulting therefrom Expired GB637863A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US637863XA 1946-02-19 1946-02-19

Publications (1)

Publication Number Publication Date
GB637863A true GB637863A (en) 1950-05-31

Family

ID=22051478

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4726/47A Expired GB637863A (en) 1946-02-19 1947-02-18 Improvements in or relating to process of preparing new quinoline antimalarial compounds and the compounds resulting therefrom

Country Status (1)

Country Link
GB (1) GB637863A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1163833B (en) * 1957-01-09 1964-02-27 Sterling Drug Inc., New York, N. Y. (V. St. A.) Process for the preparation of 6-methoxy-8- (4-n-propylamino-pentylamino) -quinoline suitable for combating malaria diseases or its non-toxic acid salts.
CN108947851A (en) * 2018-08-02 2018-12-07 中国科学院兰州化学物理研究所苏州研究院 A kind of synthetic method of 5- amino -1- amylalcohol

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1163833B (en) * 1957-01-09 1964-02-27 Sterling Drug Inc., New York, N. Y. (V. St. A.) Process for the preparation of 6-methoxy-8- (4-n-propylamino-pentylamino) -quinoline suitable for combating malaria diseases or its non-toxic acid salts.
CN108947851A (en) * 2018-08-02 2018-12-07 中国科学院兰州化学物理研究所苏州研究院 A kind of synthetic method of 5- amino -1- amylalcohol
CN108947851B (en) * 2018-08-02 2020-12-11 中国科学院兰州化学物理研究所苏州研究院 Synthesis method of 5-amino-1-pentanol

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