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GB735547A - Substituted 8-quinolinols - Google Patents

Substituted 8-quinolinols

Info

Publication number
GB735547A
GB735547A GB1602653A GB1602653A GB735547A GB 735547 A GB735547 A GB 735547A GB 1602653 A GB1602653 A GB 1602653A GB 1602653 A GB1602653 A GB 1602653A GB 735547 A GB735547 A GB 735547A
Authority
GB
United Kingdom
Prior art keywords
dimethylaminomethyl
quinolinol
quinolinols
reaction
acetyl
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
GB1602653A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB735547A publication Critical patent/GB735547A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • 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
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

The invention comprises 5-acyl-7-tertiary aminomethyl-8-quinolinols, in which the 5-substituent contains an aryl or heterocyclic radical attached directly or through an alkyl radical to the C-atom of the CO group. The tertiary amino group may contain 2 similar or different alkyl groups with or without hetero-atoms, and which may be substituted, or which may together form a saturated heterocyclic ring with the N; also a method of obtaining them by reaction of the 5-acyl-8-quinolinol with formaldehyde and a secondary amine or by reaction of an aromatic or heterocyclic aldehyde with 5-acetyl-8-quinolinol substituted as above by a tertiary aminomethyl radical. In examples, 5 - benzoyl - 8 - quinolinol, the corresponding para - chloro, 21 - chloro -, and 21 - 41 - dichloro benzoyl - 8 - quinolinols are treated with dimethylamine and formaldehyde, to give the corresponding 5-benzoyl or -chlorobenzoyl - 7 - dimethylaminomethyl - 8 - quinolinols; 5 - cinnamoyl - 8 - quinolinol reacts similarly with corresponding amines, to give the 7 - dimethylaminomethyl compound, the 7-di - N : N1 - p - hydroxyethyl - and the 7-diethylaminomethyl compound; and the preparation of other derivatives including the 7-(1 - piperidyl)methyl -, 7(4 - methyl - 1-piperazyl ,- 7 - methyl - N - n - dodecylaminomethyl -, 7 - (1 - pyrrolidyl)methyl -, 7 - N : N1-bis(b - diethylaminoethyl)aminomethyl -, and the N - ethyl - N(b - diethylaminoethyl) aminomethyl - compounds, is described; the 5 - o - cinnamal - acetyl - 7 - dimethylaminomethyl, 5 - b - phenylpropionyl - 7 - dimethylaminomethyl -, 5 - benzoylacetyl - 7 - dimethylaminomethyl -, are also specified; other products specified include 7-dimethylaminomethyl-8-quinolinols having in the 5-position the following groups: 3 : 4 dimethoxycinnamoyl-, furfurylideneacetyl -, 5-nitrofurfurylideneacetyl-and 6-quinolylidene acetyl, and a table gives the amoebicidal activity of several of the products. The second method of reaction is exemplified by the reaction between 5-acetyl-7-dimethylaminomethyl-8-quinolinol and benzaldehyde to give the corresponding 5-cinnamoyl-derivative. 5-Acyl-8-quinolinols may be obtained by a Friedel-Craft reaction between an acylchloride and 8-quinolinol.
GB1602653A 1952-06-11 1953-06-10 Substituted 8-quinolinols Expired GB735547A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF9240A DE1039518B (en) 1952-06-11 1952-06-11 Process for the preparation of basic substituted 8-oxyquinolines

Publications (1)

Publication Number Publication Date
GB735547A true GB735547A (en) 1955-08-24

Family

ID=7086074

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1602653A Expired GB735547A (en) 1952-06-11 1953-06-10 Substituted 8-quinolinols

Country Status (4)

Country Link
CH (2) CH319788A (en)
DE (1) DE1039518B (en)
FR (1) FR1086808A (en)
GB (1) GB735547A (en)

Also Published As

Publication number Publication date
CH319778A (en) 1957-02-28
FR1086808A (en) 1955-02-16
DE1039518B (en) 1958-09-25
CH319788A (en) 1957-02-28

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