GB705878A - Heterocyclic nitrogen compounds and methods for obtaining the same - Google Patents

Heterocyclic nitrogen compounds and methods for obtaining the same

Info

Publication number
GB705878A
GB705878A GB1544/52A GB154452A GB705878A GB 705878 A GB705878 A GB 705878A GB 1544/52 A GB1544/52 A GB 1544/52A GB 154452 A GB154452 A GB 154452A GB 705878 A GB705878 A GB 705878A
Authority
GB
United Kingdom
Prior art keywords
quinolinol
chloro
diethylaminomethyl
methyl
amine
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
GB1544/52A
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.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
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 Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Publication of GB705878A publication Critical patent/GB705878A/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
    • C07D215/20—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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention comprises halogenated-7-substituted aminomethyl - 8 - quinolinol compounds of the formula <FORM:0705878/IV (b)/1> where x is a halogen atom, and R1 and R2 are alike or different and represent alkyl or hydroxyalkyl radicals, or, when taken together with -N<, a saturated heterocyclic ring, and acid addition salts of such compounds. They are obtained by condensing a compound of the formula <FORM:0705878/IV (b)/2> with formaldehyde and an amine of formula HNR1R2 or an acid addition salt of such amine or with the product obtained by condensing the amine or acid addition salt thereof and formaldehyde. The groups R1 and R2 contain not more than 4 carbon atoms. Reaction may be effected in an alcoholic solvent. Salts mentioned are the hydrochloride, hydrobromide, hydroiodide, sulphate, sulphamate, phosphate, citrate, acetate and tartrate. Strong mineral acids yield mono- and di-salts. In example (1) 5-chloro-7-diethylaminomethyl-8-quinolinol is obtained by reacting 5-chloro-8-quinolinol, paraformaldehyde and diethylamine and is converted to its hydrochloride, hydrobromide, and phosphate. Similarly prepared from paraformaldehyde and the appropriate amines and halogen-substituted quinolinols are (2) 5-chloro-7-dimethylaminomethyl - 8 - quinolinol; (3) 5-chloro-7-(4-morpholinomethyl) and (1 - piperidylmethyl) - 8 - quinolinols; (4) 5 - chloro - 7 - (ethyl - b - hydroxyethylamino methyl) - 8 - quinolinol; (5) 5 - chloro - 7 - (di - n - propylamino - methyl) - 8 - quinolinol; (6) 5 - chloro - 7 - (di - n - butyl - aminomethyl) - 8 - quinolinol; (7) 5 - bromo - 7 - diethylaminomethyl - 8 - quinolinol; (8) 6 - chloro - 7 - (1 - piperidyl - methyl) - 8 - quinolinol; (9) 5 - bromo - 7 - methyl - ethylaminomethyl) - 8 - quinolinol; (10) 5 - chloro - 7 - (1 - pyrrolidinylmethyl) - 8 - quinolinol; (11) 6 - chloro - 7 - dimethyl - aminomethyl - 8 - quinolinol; (12) 6 - chloro - 7 - diethylaminomethyl - 8 - quinolinol; (13) 5 - fluoro - 7 - diethylaminomethyl - 8 - quinolinol, mostly as their mono- or di-hydrochlorides.
GB1544/52A 1951-02-13 1952-01-18 Heterocyclic nitrogen compounds and methods for obtaining the same Expired GB705878A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US705878XA 1951-02-13 1951-02-13

Publications (1)

Publication Number Publication Date
GB705878A true GB705878A (en) 1954-03-17

Family

ID=22096220

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1544/52A Expired GB705878A (en) 1951-02-13 1952-01-18 Heterocyclic nitrogen compounds and methods for obtaining the same

Country Status (1)

Country Link
GB (1) GB705878A (en)

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