GB457621A - Improvements in the manufacture and production of condensation products - Google Patents

Improvements in the manufacture and production of condensation products

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Publication number
GB457621A
GB457621A GB2139335A GB2139335A GB457621A GB 457621 A GB457621 A GB 457621A GB 2139335 A GB2139335 A GB 2139335A GB 2139335 A GB2139335 A GB 2139335A GB 457621 A GB457621 A GB 457621A
Authority
GB
United Kingdom
Prior art keywords
cyanoethyl
yields
products
dimethylindole
methylindole
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
GB2139335A
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
Priority to GB2139335A priority Critical patent/GB457621A/en
Publication of GB457621A publication Critical patent/GB457621A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C07D207/327—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • 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
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

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

Abstract

N-(o -cyanoethyl) derivatives of compounds containing one or more NH groups in heterocyclic combination are prepared by treating such compounds with acrylic nitrile in an alkaline medium. Specified heterocyclic starting materials are pyrrole and its hydrogenation products and C-substitution products, such as 2-methylpyrrole, indole and its hydrogenation products and C-substitution products, such as 2 : 3-dihydroindole, 2-phenylindole, 2-, 3- or 5-methylindole, and 2 : 3-dimethylindole, carbazole and its hydrogenation products and C-substitution products, such as tetra- and hexa - hydrocarbazole, tetrahydroquinoline, tetrahydroisoquinoline, piperidine, imidazole and its substitution products, such as benzimidazole, dihydroacridine, morpholine, perimidine and C-methylperimidines, hydrogenated thiazines such as thiodiphenylamine, piperazine, hydropyrimidines and hydroperimidines. As agents for rendering the medium alkaline, use may be made of alkali oxides, hydroxides, alcoholates, phenolates or naphtholates or of free alkali metals, but when the heterocyclic starting material, e.g. piperidine, is sufficiently strongly alkaline, addition of another alkaline agent may be unnecessary. Substances which promote the reaction and/or restrain the nitrile from polymerizing may be present, mention being made of copper compounds, such as copper acetate, oleate or borate or cuprous chloride, and phenols such as phenol, hydroquinone or resorcinol. The reaction is preferably effected at a raised temperature and at atmospheric or raised pressure in a solvent or diluent which may be an excess of acrylic nitrile, an alcohol such as butanol, a hydrocarbon such as benzine, benzene or cyclohexane, pyridine, acetonitrile, or ethyl acetate. The products may be converted into the corresponding carboxylic acids or their salts or amides by saponification, or into amines by catalytic hydrogenation, or into esters by acid saponification in the presence of an alcohol; the esters may also be obtained by way of the free acids. Examples are given in which, by addition of acrylic nitrile, (1) pyrrole yields N-(o -cyanoethyl)pyrrole; (2) piperidine yields N-(o -cyanoethyl)piperidine; (3) 2-methylindole yields N-(o -cyanoethyl)-2-methylindole and, as a by-product N : 3-di(o -cyanoethyl)-2-methylindole; these products may be saponified to yield the corresponding mono- and di-carboxylic acids; (4) 2-phenylindole yields N-(o -cyanoethyl)-2-phenylindole, which may be saponified to yield the corresponding acid; N : 3-di(o -cyanoethyl) - 2 - phenylindole may also be obtained; (5) carbazole yields N-(o -cyanoethyl)carbazole, which may be saponified to yield the corresponding acid; (6) decahydroquinoline yields N-(o -cyanoethyl)decahydroquinoline; (7) perimidine yields N-(o -cyanoethyl)perimidine; (8) indole yields N-(o -cyanoethyl)indole; (9) piperazine yields N : N<1>-di(o -cyanoethyl)piperazine; (10) 2 : 3-dimethylindole yields N-(o -cyanoethyl)-2 : 3-dimethylindole; (11) 5-methoxy-2 : 3-dimethylindole yields N - (o - cyanoethyl) - 5 - methoxy - 2 : 3-dimethylindole; (12) benzimidazole yields N-(o -cyanoethyl)benzimidazole.
GB2139335A 1935-07-27 1935-07-27 Improvements in the manufacture and production of condensation products Expired GB457621A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2139335A GB457621A (en) 1935-07-27 1935-07-27 Improvements in the manufacture and production of condensation products

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2139335A GB457621A (en) 1935-07-27 1935-07-27 Improvements in the manufacture and production of condensation products

Publications (1)

Publication Number Publication Date
GB457621A true GB457621A (en) 1936-12-02

Family

ID=10162160

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2139335A Expired GB457621A (en) 1935-07-27 1935-07-27 Improvements in the manufacture and production of condensation products

Country Status (1)

Country Link
GB (1) GB457621A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2415453A (en) * 1944-01-10 1947-02-11 Universal Oil Prod Co Synthesis of bicyclo-olefinic compounds
US2431463A (en) * 1942-06-25 1947-11-25 American Cyanamid Co Vitamin b intermediates
US2446957A (en) * 1943-01-14 1948-08-10 Du Pont Process for producing nicotinamide
US2453496A (en) * 1943-10-19 1948-11-09 James F Couch Process of converting nicotinonitrile into nicotinamide
US2461842A (en) * 1943-02-26 1949-02-15 Sharples Chemicals Inc Condensation of nitriles with amides and the production of beta-alanine
US2577477A (en) * 1951-12-04 Tetracyanoethyl benzoguanamine
US2774758A (en) * 1954-08-05 1956-12-18 Monsanto Chemicals Morpholine derivative
US3042672A (en) * 1962-07-03 Chschacn

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2577477A (en) * 1951-12-04 Tetracyanoethyl benzoguanamine
US3042672A (en) * 1962-07-03 Chschacn
US2431463A (en) * 1942-06-25 1947-11-25 American Cyanamid Co Vitamin b intermediates
US2446957A (en) * 1943-01-14 1948-08-10 Du Pont Process for producing nicotinamide
US2461842A (en) * 1943-02-26 1949-02-15 Sharples Chemicals Inc Condensation of nitriles with amides and the production of beta-alanine
US2453496A (en) * 1943-10-19 1948-11-09 James F Couch Process of converting nicotinonitrile into nicotinamide
US2415453A (en) * 1944-01-10 1947-02-11 Universal Oil Prod Co Synthesis of bicyclo-olefinic compounds
US2774758A (en) * 1954-08-05 1956-12-18 Monsanto Chemicals Morpholine derivative

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