GB693353A - Process for the preparation of 2-aminoquinoxalines - Google Patents

Process for the preparation of 2-aminoquinoxalines

Info

Publication number
GB693353A
GB693353A GB26814/49A GB2681449A GB693353A GB 693353 A GB693353 A GB 693353A GB 26814/49 A GB26814/49 A GB 26814/49A GB 2681449 A GB2681449 A GB 2681449A GB 693353 A GB693353 A GB 693353A
Authority
GB
United Kingdom
Prior art keywords
amino
prepared
nitrile
hydrogen
glycolonitrile
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
GB26814/49A
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.)
Merck and Co Inc
Original Assignee
Merck and Co 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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB693353A publication Critical patent/GB693353A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring

Landscapes

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

Abstract

2-Aminoquinoxaline compounds of formula: <FORM:0693353/IV (b)/1> where R1 and R2 are hydrogen, halogen, alkyl or alkoxy, are prepared by treating the N-(o-aminophenyl) glycine nitrile <FORM:0693353/IV (b)/2> with a methanolic solution of a strong base to cyclize it and then oxidizing the resultant 3 : 4-dihydroquinoxaline derivative. The above substituted glycine nitrile may be prepared by treating a 1 : 2 diaminobenzene with a haloacetonitrile, a mixture of formaldehyde and hydrogen cyanide, or glycolonitrile. R1 and R2 may be chloro, methyl, ethyl, isopropyl, methoxy, ethoxy, or propoxy and examples are given of compounds with these substituents. In the examples, o-phenylenediamine is treated with formaldehyde-bisulphite complex and hydrogen cyanide to give N-(o-aminophenyl) glycine nitrile (alternatively glycolonitrile or chloroacetonitrile are employed), and this nitrile is treated with sodium methoxide in methanol to give 2-amino-3 : 4-dihydroquinoxaline, which is oxidized under various conditions (e.g. with hydrogen peroxide) to afford 2-aminoquinoxaline. In a similar way there are prepared 2-amino-methylquinoxalines, 2-aminochloroquinoxalines, and 2-amino-methoxyquinoxalines.
GB26814/49A 1948-10-23 1949-10-19 Process for the preparation of 2-aminoquinoxalines Expired GB693353A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US693353XA 1948-10-23 1948-10-23

Publications (1)

Publication Number Publication Date
GB693353A true GB693353A (en) 1953-07-01

Family

ID=22088284

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26814/49A Expired GB693353A (en) 1948-10-23 1949-10-19 Process for the preparation of 2-aminoquinoxalines

Country Status (1)

Country Link
GB (1) GB693353A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110105294A (en) * 2019-06-24 2019-08-09 西南大学 A kind of preparation method of polysubstituted tetrahydroquinoxaline derivative

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110105294A (en) * 2019-06-24 2019-08-09 西南大学 A kind of preparation method of polysubstituted tetrahydroquinoxaline derivative

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