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GB916103A - Process for the production of 2,4-dioxy-quinolines - Google Patents

Process for the production of 2,4-dioxy-quinolines

Info

Publication number
GB916103A
GB916103A GB2566960A GB2566960A GB916103A GB 916103 A GB916103 A GB 916103A GB 2566960 A GB2566960 A GB 2566960A GB 2566960 A GB2566960 A GB 2566960A GB 916103 A GB916103 A GB 916103A
Authority
GB
United Kingdom
Prior art keywords
quinoline
dioxy
malonic acid
prepared
acid bis
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
GB2566960A
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur 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 Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Publication of GB916103A publication Critical patent/GB916103A/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
    • C07D215/22—Oxygen atoms attached in position 2 or 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms

Landscapes

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

Abstract

2:4-dihydroxy quinolines are prepared by reacting a polyphosphoric acid with a malonic acid dianilide, which may be substituted in the methylene group or in the aromatic p nuclei, at an elevated temperature. The polyphosphoric acids used may be those prepared by heating orthophosphoric acid with P2O5, if desired in situ. Examples describe the conversion of (1) malonic acid dianilide into 2:4-dioxy quinoline; (2) malonic acid bis-p-chloranilide into 2:4-dioxy-6-chloro quinoline; (3) malonic acid bis(2,5-dichlor anilide) into 2:4-dioxy-5:8-dichloro quinoline; (4) malonic acid bis(p-toluidide) into 2:4-dioxy-6-methyl quinoline and a small amount of 4-p-toluidino-2-hydroxy-6-methyl quinoline; and (5) malonic acid bis-(p-anisidide) into 2:4-dioxy-6-methoxy quinoline, in each case the reaction being effected at 140 DEG -150 DEG C. and the product isolated by pouring the reaction mixture into water. It is stated that, in similar manner, 2:4-xioxy-3-butyl quinoline and 2:4 - dioxy-3-benzyl quinoline may be prepared from butyl and benzyl malonic acid dianilides. Specification 811,957 is referred to.
GB2566960A 1959-08-01 1960-07-22 Process for the production of 2,4-dioxy-quinolines Expired GB916103A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1959C0019530 DE1163832B (en) 1959-08-01 1959-08-01 Process for the preparation of 2,4-dihydroxy-quinolines.

Publications (1)

Publication Number Publication Date
GB916103A true GB916103A (en) 1963-01-23

Family

ID=7016639

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2566960A Expired GB916103A (en) 1959-08-01 1960-07-22 Process for the production of 2,4-dioxy-quinolines

Country Status (3)

Country Link
CH (1) CH380727A (en)
DE (1) DE1163832B (en)
GB (1) GB916103A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0335046A1 (en) * 1986-10-06 1989-10-04 Mitsubishi Kasei Corporation Method for producing 2,4-dihydroxyquinoline derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0335046A1 (en) * 1986-10-06 1989-10-04 Mitsubishi Kasei Corporation Method for producing 2,4-dihydroxyquinoline derivatives
US4904787A (en) * 1986-10-06 1990-02-27 Mitsubishi Kasei Corporation Method for producing 2,4-dihydroxyquinoline derivatives

Also Published As

Publication number Publication date
CH380727A (en) 1964-08-15
DE1163832B (en) 1964-02-27

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