GB806914A - Manufacture of basic ketones - Google Patents

Manufacture of basic ketones

Info

Publication number
GB806914A
GB806914A GB12872/55A GB1287255A GB806914A GB 806914 A GB806914 A GB 806914A GB 12872/55 A GB12872/55 A GB 12872/55A GB 1287255 A GB1287255 A GB 1287255A GB 806914 A GB806914 A GB 806914A
Authority
GB
United Kingdom
Prior art keywords
phenyl
additional values
pyridyl
lower alkyl
alkali metal
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
GB12872/55A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB806914A publication Critical patent/GB806914A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • 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
    • C07D213/50—Ketonic radicals
    • 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
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms

Landscapes

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

Abstract

Ketones of the formula <FORM:0806914/IV (b)/1> (wherein R1 is a phenyl, chlorophenyl, tolyl or methoxyphenyl, R2 is a heterocyclic radical, R3 is hydrogen or lower alkyl, R4 is lower alkyl and R5 and R6 are each lower alkyl or together with the nitrogen atom form a saturated heterocyclic radical, the lower alkyl radicals containing at most 4 carbon atoms) are prepared by reacting a compound of the formula <FORM:0806914/IV (b)/2> with a strongly basic alkali metal compound, e.g. a hydride, amide or hydrocarbon compound of an alkali metal, and then condensing the alkali metal compound so obtained with an ester (the ester group containing at most 6 carbon atoms) or a halide of the acid R4COOH. In examples: (1) sodium in ether is added to 1 - phenyl - 1 - pyridyl - (21) - 3 - dimethylaminopropane in chlorobenzene, the mixture is boiled, ethyl propionate is added and the mixture is again boiled to give, on working up, 1 - dimethylamino - 3 - phenyl - 3 - pyridyl - (21)-hexanone-(4), the maleate of which is also described; (2) 1-phenyl-1-pyridyl-(41)-3-dimethylaminopropane is boiled with sodamide in toluene, propionyl chloride is added and the mixture is heated at 95 DEG C. to give, on working up, 1 - dimethylamino - 3 - phenyl - 3 - pyridyl - (41)-hexanone-4, the maleate of which is also described. Reference is also made to other starting materials and products in which R1 has the additional values of p-methoxyphenyl, p-and o-chlorophenyl and p-tolyl, R2 the additional values of thiazolyl-(2), quinolyl-(2), quinolyl-(4), pyrimidinyl-(2) and benziminazolyl, R3 the additional values of methyl, ethyl, propyl and butyl, R5 and R6 the additional values of ethyl, propyl and butyl or, together with the nitrogen atom, of piperidino, pyrrolidino, morpholino and piperazino and R4 the additional values of methyl and isopropyl. A list of further salt forming organic and inorganic acids is also given.
GB12872/55A 1954-05-03 1955-05-03 Manufacture of basic ketones Expired GB806914A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE806914X 1954-05-03

Publications (1)

Publication Number Publication Date
GB806914A true GB806914A (en) 1959-01-07

Family

ID=6722717

Family Applications (2)

Application Number Title Priority Date Filing Date
GB12872/55A Expired GB806914A (en) 1954-05-03 1955-05-03 Manufacture of basic ketones
GB12871/55A Expired GB807757A (en) 1954-05-03 1955-05-03 Manufacture of basic carboxylic esters

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB12871/55A Expired GB807757A (en) 1954-05-03 1955-05-03 Manufacture of basic carboxylic esters

Country Status (2)

Country Link
FR (2) FR1228802A (en)
GB (2) GB806914A (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4562258A (en) * 1982-02-04 1985-12-31 Findlay John W A 6-[3-Amino-1-(4-tolyl)prop-1E-enyl]pyridine-2-carboxylic acid derivatives having antihistaminic activity
SI8310221A8 (en) * 1982-02-04 1995-10-31 Wellcome Found Process for obtaining new pyridil compounds
US4639459A (en) * 1983-02-01 1987-01-27 Burroughs Wellcome Co. Use of trifluoromethyl compounds
US4584382A (en) * 1983-02-01 1986-04-22 Findlay John W A Pyridyl acrylate compound
US4564685A (en) * 1983-03-10 1986-01-14 Findlay John W A Diphenylmethane compounds
US4621094A (en) * 1983-03-10 1986-11-04 Findlay John W A Anti-histaminic pyridyl compounds
US4690933A (en) * 1984-07-27 1987-09-01 Burroughs Wellcome Co. Pyridylvinyl-1H tetrazole having antihistamine activity

Also Published As

Publication number Publication date
GB807757A (en) 1959-01-21
FR1228802A (en) 1960-09-02
FR1228801A (en) 1960-09-02

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