GB909359A - Improvements in chlorhydroxyquinoline and the production thereof - Google Patents

Improvements in chlorhydroxyquinoline and the production thereof

Info

Publication number
GB909359A
GB909359A GB2230760A GB2230760A GB909359A GB 909359 A GB909359 A GB 909359A GB 2230760 A GB2230760 A GB 2230760A GB 2230760 A GB2230760 A GB 2230760A GB 909359 A GB909359 A GB 909359A
Authority
GB
United Kingdom
Prior art keywords
hydroxyquinoline
monochlor
weight
chlorhydroxyquinoline
dichlor
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
GB2230760A
Inventor
Patrick Joseph Campbell
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.)
ER Squibb and Sons Ltd
Original Assignee
ER Squibb and Sons 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 ER Squibb and Sons Ltd filed Critical ER Squibb and Sons Ltd
Priority to GB2230760A priority Critical patent/GB909359A/en
Priority to BR13020261A priority patent/BR6130202D0/en
Publication of GB909359A publication Critical patent/GB909359A/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
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7

Landscapes

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

Abstract

The invention comprises chlorhydroxyquinoline consisting of 57-74% by weight of 5,7-dichlor-8-hydroxyquinoline, 23-40% 5-monochlor-8-hydroxyquinoline, and 0-3% 7-monochlor-8-hydroxyquinoline; and its preparation by the action of sulphuryl chloride on 8-hydroxyquinoline in glacial acetic acid at a temperature no greater than the reflux temperature, and separation of the product. It is preferred to use a weight of sulphuryl chloride 1 1/4 to 3 times that of 8-hydroxyquinoline, to effect chlorination at 35-60 DEG C., for example agitating over 3/4 -3 hours, to arrest reaction by rapid cooling by, for example, running into distilled water, and finally to effect separation of the product by reducing the acidity, for example to pH 6 with ammonia, followed by centrifuging and washing. The defined mixture has unexpected biological activity.ALSO:A chlorhydroxyquinoline mixture consisting of 57-74% by weight of 5,7-dichlor-8-hydroxyquinoline, 23-40% 5-monochlor-8-hydroxyquinoline and 0-3% 7-monochlor-8-hydroxyquinoline has antibacterial, antiamoebic and antifungal activity. Oral administration is mentioned.
GB2230760A 1960-02-24 1960-02-24 Improvements in chlorhydroxyquinoline and the production thereof Expired GB909359A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB2230760A GB909359A (en) 1960-02-24 1960-02-24 Improvements in chlorhydroxyquinoline and the production thereof
BR13020261A BR6130202D0 (en) 1960-02-24 1961-06-22 CHLOROHYDROXYQUINOLINE PREPARATION PROCESS

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2230760A GB909359A (en) 1960-02-24 1960-02-24 Improvements in chlorhydroxyquinoline and the production thereof

Publications (1)

Publication Number Publication Date
GB909359A true GB909359A (en) 1962-10-31

Family

ID=10177270

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2230760A Expired GB909359A (en) 1960-02-24 1960-02-24 Improvements in chlorhydroxyquinoline and the production thereof

Country Status (2)

Country Link
BR (1) BR6130202D0 (en)
GB (1) GB909359A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL422265A1 (en) * 2017-07-18 2019-01-28 Valeant Pharmaceuticals Ireland Method for producing chloroquinaldol with increased purity

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL422265A1 (en) * 2017-07-18 2019-01-28 Valeant Pharmaceuticals Ireland Method for producing chloroquinaldol with increased purity

Also Published As

Publication number Publication date
BR6130202D0 (en) 1973-06-07

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