GB794870A - A process for the production of 3-oxo-2,3-dihydropyridazine derivatives - Google Patents

A process for the production of 3-oxo-2,3-dihydropyridazine derivatives

Info

Publication number
GB794870A
GB794870A GB13497/56A GB1349756A GB794870A GB 794870 A GB794870 A GB 794870A GB 13497/56 A GB13497/56 A GB 13497/56A GB 1349756 A GB1349756 A GB 1349756A GB 794870 A GB794870 A GB 794870A
Authority
GB
United Kingdom
Prior art keywords
oxo
dihydropyridazine
phenyl
ethyl
secondary amine
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
GB13497/56A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik 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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB794870A publication Critical patent/GB794870A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D237/14—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D237/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The invention comprises 3-oxo-2 : 3-dihydropyridazine derivatives of the general formula: <FORM:0794870/IV (b)/1> (wherein NR2 represents the residue of a saturated secondary amine), and the preparation thereof by condensing b -propionylpropionic acid with phenylhydrazine, subjecting the resulting 2 - phenyl - 6 - ethyl - 3 - oxo - 2 : 3 : 4 : 5 - tetrahydropyridazine to simultaneous or successive dehydrogenation and halogenation to produce a 4 - halogeno - 2 - phenyl - 6 - ethyl - 3 - oxo-2 : 3-dihydropyridazine, and exchanging the halogen therein by reaction with a saturated secondary amine. The initial condensation may be effected by heating about equimolecular amounts of the reactants, preferably in an indifferent solvent and in the presence of a base. The dehydrogenation and halogenation are preferably effected simultaneously by the action, in an inert diluent, of 3-5 molecular proportions of a phosphorus pentahalide, preferably in the presence of an aluminium halide, or of free chlorine or bromine in the presence of catalytic amounts of phosphorus pentahalide. Alternatively dehydrogenation may first be effected with chlorine, bromine or sulphuryl chloride in the absence of phosphorus penta-halide to form 2-phenyl-6-ethyl-3-oxo-2 : 3-dihydropyridazine, which is then subjected to substitution halogenation, e.g. with PCl5 or with chlorine in the presence of a small amount of PCl5. The reaction of the 4-halogeno-2-phenyl-6 - ethyl - 3 - oxo - 2 : 3 - dihydropyridazine with the secondary amine HNR2 takes place at room temperature, advantageously in a solvent, the hydrogen halide split off being preferably bound by the addition of a basic agent or the use of excess of the secondary amine. Specified saturated secondary amines, some of which are used in examples, are dimethylamine, diethylamine, methylethylamine, di-isopropylamine, pyrrolidine, piperidine, morpholine and hexamethyleneimine. Specifications 656,228 and 671,732 are referred to.
GB13497/56A 1955-05-07 1956-05-02 A process for the production of 3-oxo-2,3-dihydropyridazine derivatives Expired GB794870A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE794870X 1955-05-07

Publications (1)

Publication Number Publication Date
GB794870A true GB794870A (en) 1958-05-14

Family

ID=6710603

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13497/56A Expired GB794870A (en) 1955-05-07 1956-05-02 A process for the production of 3-oxo-2,3-dihydropyridazine derivatives

Country Status (1)

Country Link
GB (1) GB794870A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007510689A (en) * 2003-11-10 2007-04-26 ラボラトリオス・アルミラル・ソシエダッド・アノニマ Novel pyridazine-3 (2H) -one derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007510689A (en) * 2003-11-10 2007-04-26 ラボラトリオス・アルミラル・ソシエダッド・アノニマ Novel pyridazine-3 (2H) -one derivatives

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