GB736344A - 2-methyl-3-amino-4:5:6-pyridinetricarboxylic acid - Google Patents

2-methyl-3-amino-4:5:6-pyridinetricarboxylic acid

Info

Publication number
GB736344A
GB736344A GB2219/54A GB221954A GB736344A GB 736344 A GB736344 A GB 736344A GB 2219/54 A GB2219/54 A GB 2219/54A GB 221954 A GB221954 A GB 221954A GB 736344 A GB736344 A GB 736344A
Authority
GB
United Kingdom
Prior art keywords
methyl
treated
amino
give
cyano
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
GB2219/54A
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 GB736344A publication Critical patent/GB736344A/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
    • 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
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3

Landscapes

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

Abstract

The invention comprises 2-methyl-3-amino-4 : 5 : 6 - pyridinetricarboxylic acid dihydrate, and its preparation by treating a triester of 2 - methyl - 3 - cyano - 4 : 5 : 6 - pyridinetricarboxylic acid with sulphuric acid to convert the cyano group into an amide or imide (depending on the reaction temperature), followed by treatment of the product so obtained with a metal hypohalite. In examples: (1) triethyl 2 - methyl - 3 - cyano - 4 : 5 : 6 - pyridinetricarboxylate is treated with sulphuric acid (97 per cent) at 25-40 DEG C. to give triethyl 2-methyl - 3 - carboxamide - 4 : 5 : 6 - pyridine-tricarboxylate which is treated with sodium hypochlorite to give 2-methyl-3-amino-4 : 5 : 6-pyridinetricarboxylic acid; and (2) triethyl 2 - methyl - 3 - cyano - 4 : 5 : 6 - pyridinetricarboxylate is treated with sulphuric acid (97 per cent) at 85-90 DEG C. to give diethyl 2 - methyl - 3 : 4 - carboximide - 5 : 6 - pyridinedicarboxylate which is treated with sodium hypochlorite to give the product of (1). Specification 733,139 is referred to.
GB2219/54A 1951-03-16 1952-02-28 2-methyl-3-amino-4:5:6-pyridinetricarboxylic acid Expired GB736344A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US736344XA 1951-03-16 1951-03-16

Publications (1)

Publication Number Publication Date
GB736344A true GB736344A (en) 1955-09-07

Family

ID=22114873

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2219/54A Expired GB736344A (en) 1951-03-16 1952-02-28 2-methyl-3-amino-4:5:6-pyridinetricarboxylic acid

Country Status (1)

Country Link
GB (1) GB736344A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0090173A1 (en) * 1982-03-31 1983-10-05 Lonza Ag Method for the preparation of 2-aminopyridins starting from N-oxides of 2-pyridine-carbonic acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0090173A1 (en) * 1982-03-31 1983-10-05 Lonza Ag Method for the preparation of 2-aminopyridins starting from N-oxides of 2-pyridine-carbonic acids

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