GB1123230A - 5-hydroxy-6-methyl-cinchomeronitrile - Google Patents

5-hydroxy-6-methyl-cinchomeronitrile

Info

Publication number
GB1123230A
GB1123230A GB3252667A GB3252667A GB1123230A GB 1123230 A GB1123230 A GB 1123230A GB 3252667 A GB3252667 A GB 3252667A GB 3252667 A GB3252667 A GB 3252667A GB 1123230 A GB1123230 A GB 1123230A
Authority
GB
United Kingdom
Prior art keywords
alkyl
acetate
hydroxy
alkoxy
cinchomeronitrile
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
GB3252667A
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.)
Daiichi Pharmaceutical Co Ltd
Original Assignee
Daiichi Pharmaceutical Co 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
Priority claimed from JP4746365A external-priority patent/JPS4811713B1/ja
Application filed by Daiichi Pharmaceutical Co Ltd filed Critical Daiichi Pharmaceutical Co Ltd
Publication of GB1123230A publication Critical patent/GB1123230A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or 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
    • C07D263/36—One oxygen atom
    • C07D263/42—One oxygen atom attached in position 5

Landscapes

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

Abstract

<FORM:1123230/C2/1> 5 - Hydroxy - 6 - methyl - cinchomeronitrile (I) is prepared by reacting fumaronitrile with a C1- 3 alkyl (5-C1- 3 alkoxy-oxazol-4-yl) acetate (III) to yield a C1- 3 alkyl (4-C1- 3 alkoxy-5,6-dicyano - 7 - oxa - 2 - azobicyclo - (2,2,1) -hept - 2-en-3-yl) acetate (VII) which product is refluxed with a solution of a hydrogen halide in a C1- 3 alcohol to yield the corresponding C1- 3 alkyl (3-hydroxy-4,5-dicyanopyridin-2-yl) acetate (VIII) which on refluxing with a solution of an alkali metal hydroxide in a C1- 3 alcohol, affords the desired product. The starting C1- 3 alkyl (5-C1- 3 alkoxy-oxazol-4-yl) acetate may be prepared by reacting a di-C1- 3 alkyl N-formyl-asparatate with phosphorus pentoxide, preferably by heating in the presence of a solvent.
GB3252667A 1965-05-21 1966-05-17 5-hydroxy-6-methyl-cinchomeronitrile Expired GB1123230A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2959265 1965-05-21
JP4746365A JPS4811713B1 (en) 1965-08-06 1965-08-06
JP7481565 1965-12-07

Publications (1)

Publication Number Publication Date
GB1123230A true GB1123230A (en) 1968-08-14

Family

ID=27286643

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3252667A Expired GB1123230A (en) 1965-05-21 1966-05-17 5-hydroxy-6-methyl-cinchomeronitrile
GB2175766A Expired GB1123229A (en) 1965-05-21 1966-05-17 5-hydroxy-6-methyl-cinchomeronitrile

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2175766A Expired GB1123229A (en) 1965-05-21 1966-05-17 5-hydroxy-6-methyl-cinchomeronitrile

Country Status (4)

Country Link
CH (2) CH464919A (en)
DE (1) DE1670524A1 (en)
GB (2) GB1123230A (en)
NL (1) NL6607005A (en)

Also Published As

Publication number Publication date
CH456595A (en) 1968-07-31
CH464919A (en) 1968-11-15
GB1123229A (en) 1968-08-14
NL6607005A (en) 1966-11-22
DE1670524A1 (en) 1972-04-20

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