GB619241A - Improvements in or relating to the manufacture of 2:6-dimethyl-pyridine-3-carboxylic acids - Google Patents

Improvements in or relating to the manufacture of 2:6-dimethyl-pyridine-3-carboxylic acids

Info

Publication number
GB619241A
GB619241A GB3416146A GB3416146A GB619241A GB 619241 A GB619241 A GB 619241A GB 3416146 A GB3416146 A GB 3416146A GB 3416146 A GB3416146 A GB 3416146A GB 619241 A GB619241 A GB 619241A
Authority
GB
United Kingdom
Prior art keywords
phenyl
dimethyl
pyridine
methoxy
dicarbethoxy
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
GB3416146A
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.)
ERNST LUDWIG REWALD
THERAPEUTIC RES CORP OF GREAT
Original Assignee
ERNST LUDWIG REWALD
THERAPEUTIC RES CORP OF GREAT
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 ERNST LUDWIG REWALD, THERAPEUTIC RES CORP OF GREAT filed Critical ERNST LUDWIG REWALD
Priority to GB3416146A priority Critical patent/GB619241A/en
Publication of GB619241A publication Critical patent/GB619241A/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

Abstract

4 - Phenyl - 2 : 6 - dimethyl - 3 - carbalkoxy-pyridines in which the phenyl radicle may contain alkyl, alkoxy, or other inert groups, hydroxy and methoxy groups being preferred on hydrolysis and treatment with sulphuric acid yield the corresponding acids which are isolated in their free states or as hemisulphates or sulphates. Ethyl alcoholic potash is the preferred hydrolytic reagent. In examples: (1) the hemisulphate of 4-phenyl-; (2) the sulphate of 4-p-methoxy-phenyl-; (3) 4-m-methoxy-phenyl-; (4) the hemisulphate of 4-o-methoxy-phenyl-; (5) 4-p-nitro-phenyl-; (6) 4-m-nitro-phenyl- and (7) 4-p-benzamidophenyl - 2 : 6 - dimethyl - pyridine - 3 - carboxylic acid are obtained from their corresponding ethyl esters by treatment with ethyl alcoholic potash and sulphuric acid in (1) the potassium salt of the acid is isolated from the hydrolysis mixture prior to treatment with sulphuric acid. The 4-methoxy compounds may be hydrolysed to the corresponding hydroxy compounds with e.g. hydriodic or hydrobromic acid. The esters used as starting materials in examples (1) to (6) are obtained by decarboxylating the corresponding 4-phenyl-2 : 6-dimethyl-3-carbethoxy-pyridine-5-carboxylic acid obtained by the partial hydrolysis of the corresponding dicarbethoxy-ester. In (3) 4-m-methoxy-phenyl-2 : 6 - dimethyl - 3 : 5 - dicarbethoxy - pyridine is obtained by condensing m-hydroxybenzaldehyde with b -aminocrotonic ethyl ester and ethyl acetoacetate to give 4-m-hydroxy-phenyl-1 : 4 - dihydro - 2 : 6 - dimethyl - 3 : 5 - dicarbethoxy-pyridine which is acetylated and oxidised to 4-m-acetoxy-phenyl-2 : 6-dimethyl-3 : 5-dicarbethoxy-pyridine, hydrolysed to the 4-m-hydroxy-compound and methylated to the desired compound and in (7) 4-p-benzamidophenyl - 2 : 6 - dimethyl - 3 - carbethoxy-pyridine is obtained by the benzoylation of the corresponding amino compound obtained by the reduction of 4-p-nitrophenyl-2 : 6-dimethyl-3-carbethoxy-pyridine. When the phenyl group has a free 2 or 5 position the products may be cyclised to the corresponding pyrido-fluorenone. Specification 619,087 is referred to.
GB3416146A 1946-11-18 1946-11-18 Improvements in or relating to the manufacture of 2:6-dimethyl-pyridine-3-carboxylic acids Expired GB619241A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3416146A GB619241A (en) 1946-11-18 1946-11-18 Improvements in or relating to the manufacture of 2:6-dimethyl-pyridine-3-carboxylic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3416146A GB619241A (en) 1946-11-18 1946-11-18 Improvements in or relating to the manufacture of 2:6-dimethyl-pyridine-3-carboxylic acids

Publications (1)

Publication Number Publication Date
GB619241A true GB619241A (en) 1949-03-07

Family

ID=10362151

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3416146A Expired GB619241A (en) 1946-11-18 1946-11-18 Improvements in or relating to the manufacture of 2:6-dimethyl-pyridine-3-carboxylic acids

Country Status (1)

Country Link
GB (1) GB619241A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2738352A (en) * 1956-03-13 Purification of pyridine compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2738352A (en) * 1956-03-13 Purification of pyridine compounds

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