GB461425A - Carboxylic acid amides derived from aza compounds - Google Patents

Carboxylic acid amides derived from aza compounds

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Publication number
GB461425A
GB461425A GB1682035A GB1682035A GB461425A GB 461425 A GB461425 A GB 461425A GB 1682035 A GB1682035 A GB 1682035A GB 1682035 A GB1682035 A GB 1682035A GB 461425 A GB461425 A GB 461425A
Authority
GB
United Kingdom
Prior art keywords
amino
azaphenanthrene
prepared
azanaphthalene
ester
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
GB1682035A
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
Priority to DEI51921D priority Critical patent/DE635782C/en
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB337537A priority patent/GB462650A/en
Priority to GB1682035A priority patent/GB461425A/en
Priority to FR803227D priority patent/FR803227A/en
Publication of GB461425A publication Critical patent/GB461425A/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 heating aza compounds having at least 2 condensed rings and no nuclear keto groups, and no other hetero atom besides nitrogen in the molecule, the aza-nitrogen standing in a 6-membered ring, and which contain at least one reactive hydrogen atom attached to nitrogen, with esters of enolizable keto-carboxylic acids Suitable starting materials on the one hand are primary or secondary amino compounds of azanaphthalenes, azaphenanthrenes (cf. Specification 451,932), azanthracenes, diazaphenanthrenes, azatriphenylene, diaza- and triaza-triphenylenes, azachrysenes, benzazapyrenes, azaperylenes, azacarbazoles and azabenzanthracenes; and on the other hand carboxylic acid esters of the formulae R.CO.CHR<1>.X or <FORM:0461425/IV/1> wherein R is any organic radicle combined to the CO group by means of carbon, R<1> is hydrogen or an organic radicle, and X is an esterified carboxylic group. Reaction is preferably effected in a diluent. In examples the following pairs of compounds are reacted together: acetoacetic ethyl ester and 9-amino-4-azaphenanthrene, 10-amino-4-azaphenan - threne, 9-amino-1-azaphenanthrene, 5-amino-4-azaphenanthrene, 6-amino-4-azaphenanthrene, 7-amino-4-azaphenanthrene, 8-amino-4-azaphenanthrene, 3-methyl-9-amino-4-azaphenanthrene, 2-methyl-5-amino-1-azaphenanthrene, amino-3-azaphenanthrenes, 9-methylamino-4-azaphenanthrene, 5-amino-2-azanaphthalene, 3-methylamino-1-azanaphthalene, 3-8-diamino-1-azanaphthalene, 8-amino-5-nitro-1-azanaphthalene, tetrahydro-1-azanaphthalene, 7-amino-1-azaphenanthrene, monamino-6.12-diazachrysene, monaminodiazatriphenylene, 2-amino-6.7-benzo-3.5.8.10-tetrazapyrene, monamino-5.11-dimethyl-4.10-diazaperylene, 3-amino-1-azanaphthalene, 9-amino-4.8-diazaphenanthrene, or the condensation product obtained by condensing 9-amino-4-azaphenanthrene with p-nitrobenzoylacetic ester and reducing; p-chlorbenzoylacetic ester and 9-amino-4-azaphenanthrene; p-nitrobenzoylacetic ester and 9-amino-4-azaphenanthrene; 2.5-dichlorbenzoylacetic ester and 9-amino-4-azaphenanthrene; benzoylacetic ester and 5-amino-2-azanaphthalene, the reduced condensation product of acetoacetic ester and 8-amino-5-nitro-1-azanaphthalene, 9-amino-4-azaphenanthrene, 9-amino-4.8-diazaphenanthrene, amino-1-azacarbazole, monamino-6.12-diazachrysene, 2 - amino - 6.7 - benzo - 3.5.8.10 - tetrazapyrene, 8 - amino - 4 - azaphenanthrene, or 3 - amino - 1 - azanaphthalene; terephthaloyl-bis-acetic ester and 10-amino-4-azaphenanthrene, 3-, 5-, 6-, 7-, 8- or 9-amino-4-azaphenanthrene, 5-, 6- or 8-amino-1-azaphenanthrene, amino-2-azaphenanthrene, amino 1.8-diazatriphenylene, 5-amino-2-azanaphthalene, a mixture of 9-amino- and 10-amino-4-azaphenanthrenes, or a mixture of p-toluidine and 9-amino-4-azaphenanthrene; nitroterephthaloyl-bis-acetic ester and 10-amino-4-azaphenanthrene; isophthaloyl-bis-acetic ester and 10-amino-4-azaphenanthrene, 5-nitroisophthaloyl-bis-acetic ester and 10-amino-4-azaphenanthrene; chlorisophthaloyl - bis - acetic ester and amino - 9-chloro-1-azanthracene; naphthoylene - 1.5 - bis - acetic ester and 10-amino-4-azaphenanthrene or 8-amino-2-methyl-1-azanaphthalene. Aza compounds.--Aminodiazaphenanthrenes are prepared by a Skraup synthesis from mononitro or monohalogen derivatives of phenylenediamines having a reactive o-position to each of the amino groups and reducing the nitro group or replacing the halogen atom of the resulting diazaphenanthrene by the amino group. Aminoazatriphenylenes are prepared by a Skraup synthesis from 9- or 10-aminophenanthrenes, nitration and reduction; aminodiaza- and -triaza-triphenylenes are similarly prepared from 9- or 10-aminomono- or diazaphenanthrenes. Aminoazachrysenes are prepared by a Skraup synthesis from 1.5-, 1.6-or 2.6-diaminonaphthalene, nitration and reduction. Aminobenzazapyrenes are prepared by condensing 1.4-diaminoanthraquinones with acetone, nitration and reduction of the resulting product; 2-amino-6.7-benzo-3.5-8.10-tetrazapyrene is prepared by reacting 2.4-diamino-1.9-anthrapyrimidine with formamide. Aminoazaperylenes are prepared by condensing 1.5-diaminoanthraquinones with acetone and nitrating and reducing; thus 5.11-dimethyl-4.10-diazaperylene is prepared by condensing 1.5-diaminoanthraquinone with acetone in an alkaline medium and may then be nitrated and reduced. Aminoazacarbazoles are prepared by dehydrating by means of copper at elevated temperature the hexahydrocarbazoles described in Specification 360,027; an amino-1-azacarbazole is prepared by nitrating and reducing 1-azacarbazole. Aminoazabenzanthracenes are prepared by treating pyridinoanthraquinones with reducing agents and treating the products with ammonia. An amino-2-azaphenanthrene is prepared by sulphonation, replacement of the sulpho group by hydroxy and the latter by the amino group. Ketocarboxylic acid esters.--Terephthaloylbis-acetic ester, p nitroterephthaloyl-bis-acetic ester, isophthaloyl-bis-acetic ester, 5-nitroisophthaloyl-bis-acetic ester and naphthoylene-1.5-bis-acetic ester are prepared by condensing the corresponding acids with acetoacetic ester in presence of alkali.
GB1682035A 1935-06-11 1935-06-11 Carboxylic acid amides derived from aza compounds Expired GB461425A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DEI51921D DE635782C (en) 1935-06-11 1935-03-21 Process for the preparation of acid amides containing the remainder of aza compounds
GB337537A GB462650A (en) 1935-06-11 1935-06-11 Carboxylic acid amides derived from aza compounds
GB1682035A GB461425A (en) 1935-06-11 1935-06-11 Carboxylic acid amides derived from aza compounds
FR803227D FR803227A (en) 1935-06-11 1936-02-21 Process for preparing amides containing the azaderivative radical

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
GB461425A true GB461425A (en) 1937-02-11

Family

ID=10084261

Family Applications (2)

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

Country Status (3)

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DE (1) DE635782C (en)
FR (1) FR803227A (en)
GB (2) GB462650A (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
DE635782C (en) 1936-09-30
GB462650A (en) 1937-03-11
FR803227A (en) 1936-09-25

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