GB948004A - A method of manufacturing pyridine derivatives - Google Patents

A method of manufacturing pyridine derivatives

Info

Publication number
GB948004A
GB948004A GB1392760A GB1392760A GB948004A GB 948004 A GB948004 A GB 948004A GB 1392760 A GB1392760 A GB 1392760A GB 1392760 A GB1392760 A GB 1392760A GB 948004 A GB948004 A GB 948004A
Authority
GB
United Kingdom
Prior art keywords
formula
temperature
general formula
formylating agent
aldehyde
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
GB1392760A
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.)
Czech Academy of Sciences CAS
Original Assignee
Czech Academy of Sciences CAS
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 Czech Academy of Sciences CAS filed Critical Czech Academy of Sciences CAS
Publication of GB948004A publication Critical patent/GB948004A/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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/48—Aldehydo radicals

Landscapes

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

Abstract

Aldehydes of the general formula: <FORM:0948004/C2/1> in which R1 and R2 are hydrogen atoms or alkyl, aralkyl or aryl hydrocarbon groups are manufactured by condensing an unsaturated aldehyde of the general formula R1CH2 CR2=CHCHO with a secondary amine R3R4NH, in which R3 and R4 are alkyl or aryl hydrocarbon groups or are joined together forming a heterocyclic ring with the nitrogen atom, in water or in an organic solvent at a temperature between -30 DEG and +50 DEG C.; treating the resulting product of formula <FORM:0948004/C2/2> at a temperature between -30 DEG and +50 DEG C. with a formylating agent of general formula R3R4N. CHCl2, obtained by the reaction of carbonyl chloride with a disubstituted formamide R3R4NCHO, in the presence or absence of an organic solvent which may be excess disubstituted formamide; and cyclising the intermediate of formula <FORM:0948004/C2/3> by treatment with aqueous ammonia or an ammonium salt solution at a temperature between 15 DEG and 95 DEG C. Alternatively the formylating agent may be obtained by reaction of POCl3 and the disubstituted formamide. In a modification the first intermediate of formula <FORM:0948004/C2/4> may be converted into the amino diene of formula R1CH=CR2.CH=CHNR3R4 by distilling under reduced pressure before reacting it with the formylating agent. In an example crotonic aldehyde is treated with dimethylamine to give 1, 3-bis-dimethylaminobut-1-ene which is added to a reagent prepared from dimethylformamide and phosgene; and the intermediate of formula <FORM:0948004/C2/5> so formed is then heated with ammonium chloride to give nicotinic aldehyde.
GB1392760A 1959-05-29 1960-04-21 A method of manufacturing pyridine derivatives Expired GB948004A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CS317259 1959-05-29

Publications (1)

Publication Number Publication Date
GB948004A true GB948004A (en) 1964-01-29

Family

ID=5371030

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1392760A Expired GB948004A (en) 1959-05-29 1960-04-21 A method of manufacturing pyridine derivatives

Country Status (3)

Country Link
CH (1) CH411876A (en)
DE (1) DE1191378B (en)
GB (1) GB948004A (en)

Also Published As

Publication number Publication date
DE1191378B (en) 1965-04-22
CH411876A (en) 1966-04-30

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