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GB230607A - Manufacture of gamma-tetra-hydroquinolone and of intermediate products - Google Patents

Manufacture of gamma-tetra-hydroquinolone and of intermediate products

Info

Publication number
GB230607A
GB230607A GB364224A GB364224A GB230607A GB 230607 A GB230607 A GB 230607A GB 364224 A GB364224 A GB 364224A GB 364224 A GB364224 A GB 364224A GB 230607 A GB230607 A GB 230607A
Authority
GB
United Kingdom
Prior art keywords
acid
tetrahydroquinolone
yields
derivative
toluenesulpho
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
GB364224A
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.)
GEORGE ROGER CLEMO
Imperial Chemical Industries Ltd
Original Assignee
GEORGE ROGER CLEMO
British Dyestuffs Corp 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 GEORGE ROGER CLEMO, British Dyestuffs Corp Ltd filed Critical GEORGE ROGER CLEMO
Priority to GB364224A priority Critical patent/GB230607A/en
Publication of GB230607A publication Critical patent/GB230607A/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
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

g -Tetrahydroquinolone of the formula <FORM:0230607/2/1> is prepared by condensing p-toluenesulphonanilide with b -chlorpropionic acid to give p-toluenesulpho-b -phenylaminopropionic acid, and treating the latter with phosphorus oxychloride to obtain N-p-toluenesulpho-b -chlortetrahydroquinolone; upon acid hydrolysis the latter compound yields g -tetrahydroquinolone. If the ring closure is effected with phosphorus pentoxide (preferably in xylene suspension) a non-chlorinated intermediate product results. Examples are given of the method, hydrolysis being effected with a mixture of hydrochloric and acetic acids or with sulphuric acid. g -Tetrahydroquinolone is an initial material for the manufacture of drugs and photographic sensitizers. It yields a benzoyl derivative with benzoyl chloride, a hydrazone with phenylhydrazine, and a benzal derivative with benzaldehyde: it forms a nitro derivative which yields on simultaneous reduction and condensation with zinc and cyclohexanone, the hydrazone, <FORM:0230607/2/2> which, on treatment with dilute sulphuric acid, gives the tetrahydrocarbazole derivative, <FORM:0230607/2/3> g -Tetrahydroquinolone also condenses with diketones; for example with isatin it gives the acid, <FORM:0230607/2/4> which loses carbon dioxide when heated, forming the base, which latter by oxidation yields the quinoquinoline, <FORM:0230607/2/5>
GB364224A 1924-02-12 1924-02-12 Manufacture of gamma-tetra-hydroquinolone and of intermediate products Expired GB230607A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB364224A GB230607A (en) 1924-02-12 1924-02-12 Manufacture of gamma-tetra-hydroquinolone and of intermediate products

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB364224A GB230607A (en) 1924-02-12 1924-02-12 Manufacture of gamma-tetra-hydroquinolone and of intermediate products

Publications (1)

Publication Number Publication Date
GB230607A true GB230607A (en) 1925-03-19

Family

ID=9762164

Family Applications (1)

Application Number Title Priority Date Filing Date
GB364224A Expired GB230607A (en) 1924-02-12 1924-02-12 Manufacture of gamma-tetra-hydroquinolone and of intermediate products

Country Status (1)

Country Link
GB (1) GB230607A (en)

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