GB1103178A - Process for the production of an isoxazole derivative - Google Patents

Process for the production of an isoxazole derivative

Info

Publication number
GB1103178A
GB1103178A GB1470767A GB1470767A GB1103178A GB 1103178 A GB1103178 A GB 1103178A GB 1470767 A GB1470767 A GB 1470767A GB 1470767 A GB1470767 A GB 1470767A GB 1103178 A GB1103178 A GB 1103178A
Authority
GB
United Kingdom
Prior art keywords
isoxazole
carboxylic acid
hydroxy
acid
bromo
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
GB1470767A
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB1103178A publication Critical patent/GB1103178A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C07D261/12—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

3 - Hydroxy - 5 - isoxazole carboxamide is prepared by heating 3-bromo- or 3-chloroisoxazole-5-carboxylic acid with an alkanol having at most 4 carbon atoms or benzyl alcohol and an alkali metal hydroxide to form a 3 - alkoxy - 5 - isoxazole carboxylic acid having at most 4 carbon atoms in the alkyl group or 3-benzyloxy - 5 - isoxazole carboxylic acid, liberatting 3 - hydroxy - 5 - isoxazole carboxylic acid from these acids by heating with hydrobromic acid, hydrochloric acid, pyridine hydrochloride, pyridine hydrobromide or an alkyl-substituted pyridine hydrochloride or hydrobromide, and converting the 3-hydroxy-5-isoxazole carboxylic acid into 3-hydroxy-5-isoxazole carboxamide by converting it into the acid chloride and reacting the latter with ammonia. The preparation of 3-bromo-5-isoxazole propionic acid and 3-bromo-5-isoxazole carboxylic acid is described.
GB1470767A 1965-05-31 1966-05-27 Process for the production of an isoxazole derivative Expired GB1103178A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH754265A CH449625A (en) 1965-05-31 1965-05-31 Process for the preparation of 3-hydroxy-5-aminomethyl-isoxazole (5-aminomethyl-3-isoxazolol)

Publications (1)

Publication Number Publication Date
GB1103178A true GB1103178A (en) 1968-02-14

Family

ID=4326769

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1470767A Expired GB1103178A (en) 1965-05-31 1966-05-27 Process for the production of an isoxazole derivative
GB2376566A Expired GB1103177A (en) 1965-05-31 1966-05-27 Process for the production of an isoxazole derivative

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2376566A Expired GB1103177A (en) 1965-05-31 1966-05-27 Process for the production of an isoxazole derivative

Country Status (6)

Country Link
AT (2) AT258900B (en)
BE (1) BE681719A (en)
CH (2) CH449627A (en)
ES (1) ES327331A1 (en)
GB (2) GB1103178A (en)
NL (1) NL6607413A (en)

Also Published As

Publication number Publication date
AT262281B (en) 1968-06-10
ES327331A1 (en) 1967-09-16
AT258900B (en) 1967-12-11
CH449627A (en) 1968-01-15
CH449625A (en) 1968-01-15
BE681719A (en) 1966-11-28
NL6607413A (en) 1966-12-01
GB1103177A (en) 1968-02-14

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