GB680255A - 7-chloro-4-[5-(n-ethyl-n-2-hydroxyethylamino)-2-pentyl]aminoquinoline and the preparation thereof - Google Patents

7-chloro-4-[5-(n-ethyl-n-2-hydroxyethylamino)-2-pentyl]aminoquinoline and the preparation thereof

Info

Publication number
GB680255A
GB680255A GB15252/50A GB1525250A GB680255A GB 680255 A GB680255 A GB 680255A GB 15252/50 A GB15252/50 A GB 15252/50A GB 1525250 A GB1525250 A GB 1525250A GB 680255 A GB680255 A GB 680255A
Authority
GB
United Kingdom
Prior art keywords
ethyl
hydroxyethylamino
chloro
pentanone
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
GB15252/50A
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.)
STWB Inc
Original Assignee
Sterling Drug Inc
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 Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of GB680255A publication Critical patent/GB680255A/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

Abstract

The invention comprises 7-chloro-4-[5-(N-ethyl - N - 2 - hydroxyethylamino) - 2 - pentyl]-aminoquinoline and acid addition salts thereof, and a method of preparing said compounds by heating 5-(N-ethyl-N-2-hydroxyethylamino)-2-pentylamine with a 4-halo-7-chloroquinoline preferably in the presence of phenol, and if necessary, converting the resulting base into acid addition salts thereof, or by heating a 1-halo-4-pentanone, e.g. 1-chloro-4-pentanone, with N-ethyl-N-hydroxyethylamine to yield 1 - (N - ethyl - N - 2 - hydroxyethylamino) - 4 - pentanone which is reductively aminated to 5-(N-ethyl-N-2-hydroxyethylamino)-2-pentylamine by contacting it with an excess of ammonia and hydrogen under pressure in the presence of a hydrogenation catalyst and the process is completed as above. 4-Halo-7-chloroquinolines that may be used are 4,7-dichloro-, 4-bromo-7-chloro- and 4-iodo-7-chloro-quinolines. Acids mentioned for salt formation are phosphoric, hydrochloric, hydrobromic, sulphuric sulphamic, tartaric, citric, succinic, acetic, benzoic and oleic acids. In the example, the above substituted quinoline and the diphosphate salt are prepared.
GB15252/50A 1949-07-23 1950-06-19 7-chloro-4-[5-(n-ethyl-n-2-hydroxyethylamino)-2-pentyl]aminoquinoline and the preparation thereof Expired GB680255A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US680255XA 1949-07-23 1949-07-23

Publications (1)

Publication Number Publication Date
GB680255A true GB680255A (en) 1952-10-01

Family

ID=22079948

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15252/50A Expired GB680255A (en) 1949-07-23 1950-06-19 7-chloro-4-[5-(n-ethyl-n-2-hydroxyethylamino)-2-pentyl]aminoquinoline and the preparation thereof

Country Status (1)

Country Link
GB (1) GB680255A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3136769A (en) * 1961-03-28 1964-06-09 Parke Davis & Co Quinoline nu-oxides
CN104803859A (en) * 2015-04-17 2015-07-29 武汉瑞凯兴科技有限公司 Synthetic method of 5-(N-ethyl-N-2-ethylol amine)-2-amylamine
CN109456266A (en) * 2018-11-12 2019-03-12 南京天际联盟医药科技有限公司 The novel preparation method of hydroxychloroquine sulfate

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3136769A (en) * 1961-03-28 1964-06-09 Parke Davis & Co Quinoline nu-oxides
CN104803859A (en) * 2015-04-17 2015-07-29 武汉瑞凯兴科技有限公司 Synthetic method of 5-(N-ethyl-N-2-ethylol amine)-2-amylamine
CN109456266A (en) * 2018-11-12 2019-03-12 南京天际联盟医药科技有限公司 The novel preparation method of hydroxychloroquine sulfate

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