GB462650A - Carboxylic acid amides derived from aza compounds - Google Patents

Carboxylic acid amides derived from aza compounds

Info

Publication number
GB462650A
GB462650A GB337537A GB337537A GB462650A GB 462650 A GB462650 A GB 462650A GB 337537 A GB337537 A GB 337537A GB 337537 A GB337537 A GB 337537A GB 462650 A GB462650 A GB 462650A
Authority
GB
United Kingdom
Prior art keywords
prepared
ester
amino
condensing
carboxylic acid
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
GB337537A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Publication of GB462650A publication Critical patent/GB462650A/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
    • C07D215/16—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 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
    • C07D215/38—Nitrogen atoms
    • 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
    • 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
    • C07D215/16—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 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
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/08—Aza-anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
    • C09B29/33—Aceto- or benzoylacetylarylides
    • C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
    • C09B29/338—Heterocyclic arylides, e.g. acetoacetylaminobenzimidazolone
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/16—Benz-diazabenzanthrones, e.g. anthrapyrimidones

Landscapes

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

Abstract

Carboxylic acid amides derived from aza compounds are prepared by condensing esters of enolizable keto-carboxylic acids of monoaza compounds, the aza nitrogen atom of which is in a six-membered ring and which contain no other hetero atom besides nitrogen, with compounds containing at least one reactive hydrogen atom attached to nitrogen. The acid-esters used as starting materials correspond to the formul <FORM:0462650/IV/1> wherein R is the residue of a monaza compound as specified above, R<1> is hydrogen or an alkyl group and X is an esterified carboxylic acid group. Compounds of which R is the residue, which are mentioned are azanaphthalenes, azaphenanthrenes (cf. Specification 451,932) azanthracenes, azatriphenylenes, (prepared by a Skraup synthesis from 9- or 10-aminophenanthrenes), azacarbazoles (prepared by dehydrating by means of copper at elevated temperatures the hexahydrocarbazoles described in Specification 360,027) and azabenzanthracenes (prepared by treating pyridinoanthraquinones with reducing agents). The enolisable keto-carboxylic acid esters thereof may be prepared from the amino compounds by diazotizing and a Sandmeyer replacement to a cyano group, saponifying, esterifying and condensing the carboxylic acid ester with the sodium compound of acetoacetic acid ethyl ester. Those esters wherein R<1> is alkyl are prepared by condensing the alkali metal compounds of those esters wherein R<1> is hydrogen with alkyl halides. In examples: 6-quinolinoyl acetic acid ester (prepared by condensing quinoline-6-carboxylic acid ester with acetic acid ethyl ester in presence of sodium ethylate and boiling benzene) is condensed with a -naphthylamine, 4-chloro-2.5-dimethoxyaniline, methylamine, ethanolamine, butylamines, octodecylamines, octodecenylamines, cyclohexylamines, aralkylamines such as phenylethylamine, tetrahydroazanaphthalene or 2-aminopyridine. Reference is also made to the condensation of pyridinoyl-acetic ester (prepared by condensing nicotinic acid ethyl ester with acetoacetic ester in presence of alkali) with 10-amino-4-azaphenanthrene or 5-amino-2-azaphenanthrene, and of quinolinoyl-5.8-bis-acetic ester or pyridinoyl-3.5-bis-acetic ester (prepared by condensing the corresponding acids with acetoacetic ester in presence of alkali) with 3-, 5-, 6-, 7-, 8-, 9-, or 10-amino-4-azaphenanthrenes, 5-, 6- or 8-amino-1-azaphenanthrenes or amino-2-azaphenanthrene (prepared from sulphonated 2-azaphenanthrene by first converting the sulpho group to hydroxy and replacing the latter by the amino group).
GB337537A 1935-06-11 1935-06-11 Carboxylic acid amides derived from aza compounds Expired GB462650A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1682035A GB461425A (en) 1935-06-11 1935-06-11 Carboxylic acid amides derived from aza compounds

Publications (1)

Publication Number Publication Date
GB462650A true GB462650A (en) 1937-03-11

Family

ID=10084261

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1682035A Expired GB461425A (en) 1935-06-11 1935-06-11 Carboxylic acid amides derived from aza compounds
GB337537A Expired GB462650A (en) 1935-06-11 1935-06-11 Carboxylic acid amides derived from aza compounds

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB1682035A Expired GB461425A (en) 1935-06-11 1935-06-11 Carboxylic acid amides derived from aza compounds

Country Status (3)

Country Link
DE (1) DE635782C (en)
FR (1) FR803227A (en)
GB (2) GB461425A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2738350A (en) * 1954-03-16 1956-03-13 Searle & Co 3-oxygenated 17alpha-aza-d-homoandrostenes and n-substituted derivatives thereof

Also Published As

Publication number Publication date
GB461425A (en) 1937-02-11
FR803227A (en) 1936-09-25
DE635782C (en) 1936-09-30

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