GB721350A - 2-methyl-3-acetyl-4:5-pyridinedicarboxylic acid and esters thereof - Google Patents

2-methyl-3-acetyl-4:5-pyridinedicarboxylic acid and esters thereof

Info

Publication number
GB721350A
GB721350A GB2647/54A GB264754A GB721350A GB 721350 A GB721350 A GB 721350A GB 2647/54 A GB2647/54 A GB 2647/54A GB 264754 A GB264754 A GB 264754A GB 721350 A GB721350 A GB 721350A
Authority
GB
United Kingdom
Prior art keywords
methyl
acid
acetyl
keto
esters
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
GB2647/54A
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB721350A publication Critical patent/GB721350A/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
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0721350/IV (b)/1> where R2 is a hydrogen atom or a hydrocarbon group and their preparation by cyclizing a N - (1 - methyl - 3 - keto - 1 - butenyl) - N - (21 : 31-dicarboxy - 31 - keto - 11 - propenyl) amine ester with concentrated sulphuric acid. The pyridine di-esters may be partly or completely hydrolysed to form the mono-acid ester or the di-acid. The group R2 is preferably a lower alkyl group of 1-6 carbon atoms. Suitably R2 may be a methyl, ethyl, propyl, butyl, benzyl or phenyl radical. In examples: (1) N - (1 - methyl - 3 - keto - 1 - butenyl) - N - (21 : 31 - dicarbethoxy - 31 - keto - 11 - propenyl) amine is treated with sulphuric acid to give diethyl 2-methyl-3-acetyl-4 : 5-pyridinedicarboxylate; (2) the process of (1) is carried out under conditions giving partial hydrolysis, to produce 2-methyl-3-acetyl-5-carbethoxy-4-pyridinecarboxylic acid; and (3) the product of (2) is further hydrolysed to give 2-methyl-3-acetyl-4 : 5 - pyridinedicarboxylic acid. Specification 721,349 is referred to.
GB2647/54A 1951-03-16 1952-03-07 2-methyl-3-acetyl-4:5-pyridinedicarboxylic acid and esters thereof Expired GB721350A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US721350XA 1951-03-16 1951-03-16

Publications (1)

Publication Number Publication Date
GB721350A true GB721350A (en) 1955-01-05

Family

ID=22105810

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2647/54A Expired GB721350A (en) 1951-03-16 1952-03-07 2-methyl-3-acetyl-4:5-pyridinedicarboxylic acid and esters thereof

Country Status (1)

Country Link
GB (1) GB721350A (en)

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