GB864208A - Novel pyridine and quinoline derivatives and the manufacture thereof - Google Patents

Novel pyridine and quinoline derivatives and the manufacture thereof

Info

Publication number
GB864208A
GB864208A GB40831/58A GB4083158A GB864208A GB 864208 A GB864208 A GB 864208A GB 40831/58 A GB40831/58 A GB 40831/58A GB 4083158 A GB4083158 A GB 4083158A GB 864208 A GB864208 A GB 864208A
Authority
GB
United Kingdom
Prior art keywords
compounds
preparation
pyridine
substituted
amino
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
GB40831/58A
Inventor
Aaron Cohen
Anthony Mesnard Parsons
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.)
Roche Products Ltd
Original Assignee
Roche Products 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 to BE585464D priority Critical patent/BE585464A/xx
Application filed by Roche Products Ltd filed Critical Roche Products Ltd
Priority to GB40831/58A priority patent/GB864208A/en
Priority to ES0254255A priority patent/ES254255A1/en
Priority to FR836059A priority patent/FR198M/en
Publication of GB864208A publication Critical patent/GB864208A/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
    • 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
    • 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

Abstract

The invention comprises compounds of the formula: <FORM:0864208/IV (b)/1> (wherein R1 and R2 are the same or different alkyl groups together containing 3 to 10 carbon atoms, or R1 and R2 together are a tetramethylene group, and R3 is amino, alkoxy or alkylamino containing at most 6 carbon atoms) and salts thereof; the preparation of the compounds wherein R3 is amino by treating an appropriate 5:6-substituted-2-hydroxy-3-cyanopyridine with POCl3, if desired in presence of a tertiary base, to give the corresponding 2-chloro compound, removing the chlorine atom with zinc and acetic acid in presence of sodium acetate and hydrolysing the resulting 5.6-substituted-3-cyano-pyridine with water in presence of a Lewis acid; the preparation of the compounds wherein R3 is alkoxy by boiling the 5:6-substituted-3-cyano-pyridine prepared as above with an alkanol in presence of a strong acid, or by reacting an appropriate 5:6-substituted-2-hydroxy-pyridine-3- carboxylic acid with POCl3 and PCl5 to give the corresponding 2-chloro-pyridine-3-carbonyl chloride, treating this with an alkanol, in an inert solvent if desired, and dechlorinating the 2-chloro-3-alkoxycarbonyl compound with hydrogen in presence of a hydrogenation catalyst or with zinc and acetic acid in presence of sodium acetate; and the preparation of the compounds wherein R3 is alkylamino by adding the 5:6-substituted-2-chloro-pyridine-3-carbonyl chloride to an excess of an appropriate alkylamine, in an inert solvent if desired, and dechlorinating the resulting amide in the manner indicated above. Examples describe the preparation of the compounds of the above general formula wherein R1 and R2 are tetranethylene and R3 is amino, methylamino and ethoxy by all the above described methods and the preparation of the compounds wherein R1 is methyl and R2 is ethyl and R3 is amino and ethoxy by the first method described above. Hydrochlorides, hydrobromides, perchlorates, methiodides and methosulphates of the products are described and the preparation of 5:6:7:8-tetrahydroquinoline-(3)-carboxylic acid hydrazide is also referred to. 5:6-Disubstituted- 2-hydroxy- 3-carboxypyridines are prepared by hydrolysis of the corresponding 3-cyano-compounds.
GB40831/58A 1958-12-18 1958-12-18 Novel pyridine and quinoline derivatives and the manufacture thereof Expired GB864208A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE585464D BE585464A (en) 1958-12-18
GB40831/58A GB864208A (en) 1958-12-18 1958-12-18 Novel pyridine and quinoline derivatives and the manufacture thereof
ES0254255A ES254255A1 (en) 1958-12-18 1959-12-17 Novel pyridine and quinoline derivatives and the manufacture thereof
FR836059A FR198M (en) 1958-12-18 1960-08-18 Pyridine derivatives.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB40831/58A GB864208A (en) 1958-12-18 1958-12-18 Novel pyridine and quinoline derivatives and the manufacture thereof

Publications (1)

Publication Number Publication Date
GB864208A true GB864208A (en) 1961-03-29

Family

ID=10416849

Family Applications (1)

Application Number Title Priority Date Filing Date
GB40831/58A Expired GB864208A (en) 1958-12-18 1958-12-18 Novel pyridine and quinoline derivatives and the manufacture thereof

Country Status (4)

Country Link
BE (1) BE585464A (en)
ES (1) ES254255A1 (en)
FR (1) FR198M (en)
GB (1) GB864208A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107876016A (en) * 2017-11-19 2018-04-06 西安元创化工科技股份有限公司 A kind of low temperature liquid phase antichlor and its preparation method and application

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107876016A (en) * 2017-11-19 2018-04-06 西安元创化工科技股份有限公司 A kind of low temperature liquid phase antichlor and its preparation method and application
CN107876016B (en) * 2017-11-19 2020-06-26 西安元创化工科技股份有限公司 Low-temperature liquid-phase dechlorinating agent and preparation method and application thereof

Also Published As

Publication number Publication date
BE585464A (en)
ES254255A1 (en) 1960-06-01
FR198M (en) 1961-02-20

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