DE850007C - Process for the preparation of N-aryl-ª ‡ -pyrrolidones - Google Patents

Process for the preparation of N-aryl-ª ‡ -pyrrolidones

Info

Publication number
DE850007C
DE850007C DEB13140A DEB0013140A DE850007C DE 850007 C DE850007 C DE 850007C DE B13140 A DEB13140 A DE B13140A DE B0013140 A DEB0013140 A DE B0013140A DE 850007 C DE850007 C DE 850007C
Authority
DE
Germany
Prior art keywords
parts
aryl
pyrrolidones
preparation
acid chloride
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
DEB13140A
Other languages
German (de)
Inventor
Heinrich Dr Hopff
Hermann Dr Spaenig
Georg Dr Triem
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEB13140A priority Critical patent/DE850007C/en
Application granted granted Critical
Publication of DE850007C publication Critical patent/DE850007C/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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom

Landscapes

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

Description

Verfahren zur Herstellung von N-Aryl-a-pyrrolidonen Fs wurde gefunde». claß man N-Aryl-a,-pyrrol- idone erhalt, 1i,-e»tt man aromatische Amine mit #,-Cltlorl>ttttersiiurechlorid umsetzt und die erhal- tenen ;,-Cltlorhttttersäurearylamide mit Alkalien behandelt. Die Umsetzung erfolgt nach dem allgemeinen Schema Dabei lwdetitet R-N I1., z. ß. Anilin, ein Toluidin, N@,licli» o(kr \al#htlivlamin, ein Chlor-. Brom-, Fluor- oder Nitroanilin, eine aromatische Aminocarlxin:iittre oder deren Salze, einen aromatischen Aminoaldehyd, ein Aminophenol oder -naphthoi, eine aromatische Aminophenolcarbonsäure oder deren Salze oder ein N, N-Dialkylphenylendiamin.Process for the preparation of N-aryl-a-pyrrolidones Fs was found ». let N-aryl-a, -pyrrole- idone receives, 1i, -e »t aromatic amines with #, - Cltlorl> adtteric acid chloride converts and the obtained tenen;, - Cltlorhttttersäurearylamide treated with alkalis. The implementation takes place according to the general scheme RN I1., Z. ß. Aniline, a toluidine, N @, licli »o (kr \ al # htlivlamin, a chlorine, bromine, Fluoro- or nitroaniline, an aromatic aminocarlxine or its salts, an aromatic aminoaldehyde, an aminophenol or naphthoi, an aromatic aminophenolcarboxylic acid or its salts or an N, N-dialkylphenylenediamine.

Die Umsetzung des aromatischen Amins mit dem y-Chlorbuttersäurechlorid wird zweckmäßig in einem indifferenten Lösungs- oder Verdünnungsmittel, wie Benzol, Toluol oder Äther, ausgeführt. Sie erfolgt meistens unter Wärmeentwicklung, so daß unter Umständen Kühlung erforderlich ist; man führt sie nötigenfalls unter Erwärmen zu Ende.The reaction of the aromatic amine with the γ-chlorobutyric acid chloride is expedient in an inert solvent or diluent, such as benzene, Toluene or ether. It usually takes place with the development of heat, so that cooling may be required; if necessary, they are carried out with heating over.

Für die zweite Stufe der Reaktion, den Ringschluß, ist es im allgemeinen nicht nötig, das in der ersten Stufe erhaltene y-Chlorbuttersäurearylamid als solches zu isolieren. Man kann vielmehr ohne weiteres die erforderliche Menge Alkali, , z. B. wäßrige Natronlauge, einrühren und erhält dabei rasch, meistens ohne Wärmezufuhr, das gewünschte N-Aryl-a-pyrrolidon. Falls das angewendete aromatische Amin noch alkalilösliche Gruppen, wie Hydroxyl-'oder Carboxylgruppen, enthält, verwendet man zweckmäßig so viel Alkali, daß das N-Ary#1-a-pyrrolidonderivat sich in der wäßrigen Alkalilauge löst; man gewinnt das gewünschte Produkt dann durch Ansäuern, der alkalischen Lösung.For the second stage of the reaction, ring closure, it is generally not necessary, the γ-chlorobutyric acid arylamide obtained in the first stage as such to isolate. Rather, one can easily use the required amount of alkali, z. B. aqueous sodium hydroxide solution, stir in and get it quickly, usually without heat, the desired N-aryl-a-pyrrolidone. If the aromatic amine used is still Alkali-soluble groups, such as hydroxyl or carboxyl groups, are used expediently so much alkali that the N-ary # 1-a-pyrrolidone derivative is in the aqueous Alkali solution dissolves; the desired product is then obtained by acidification, the alkaline one Solution.

Die N-Aryl-a-pyrrolidone dienen als Zwischenprodukte für Farbstoffe und pharmazeutische Produkte.The N-aryl-a-pyrrolidones serve as intermediates for dyes and pharmaceutical products.

Die in den Beispielen genannten Teile sind Gewichtsteile. Beispiel i 85 Teile p-aminobenzoesaures Natrium werden in 5oo Teilen Benzol suspendiert und unter Rühren mit 7o Teilen y-Chlorbuttersäurechlorid versetzt. Das Reaktionsgemisch erwärmt sich auf 6o°. Es wird bei dieser Temperatur 20 Stunden weitergerührt. N aem Abkühlen auf gewöhnliche Temperatur läßt man 5oo Teile 2oo/oige Natronlauge zufließen. Man trennt das Benzol von der wäßrigen Lösung ab und fällt, nachdem die wäßrige Lösung mit Tierkohle geklärt ist, die N-Phenyl-a-pyrrolidon-4 -carbonsäure durch Ansäuern aus. Man kristallisiert sie aus Methanol um und erhält 8o Teile farblose Kristalle vom F. 244 liis 245°.The parts mentioned in the examples are parts by weight. example 85 parts of sodium p-aminobenzoate are suspended in 500 parts of benzene and 70 parts of γ-chlorobutyric acid chloride are added with stirring. The reaction mixture heats up to 60 °. Stirring is continued at this temperature for 20 hours. N After cooling to the usual temperature, 500 parts of 2oo% sodium hydroxide solution are left flow in. The benzene is separated from the aqueous solution and precipitated after the aqueous solution is clarified with animal charcoal, the N-phenyl-a-pyrrolidone-4-carboxylic acid by acidification. It is recrystallized from methanol and 80 parts of colorless material are obtained Crystals from m. 244 to 245 °.

Beispiel 2 211 Teile des Natriumsalzes der 2-Oxy-4-aminobenzoesäure werden in 5oo Teilen Benzol suspendiert und unter Rühren mit 14 Teilen y-Chlorbuttersäurechlorid versetzt. Das Reaktionsgemisch erwärmt sich auf 70°. Es wird bei dieser Temperatur 2 Stunden weitergerührt. Man verfährt dann weiter wie im Beispiel i und erhält 16o Teile N-(4 -Carboxy-3'-oxy#1)@lienyl) -a-liyrrolidon, (las nach dem Umkristallisieren aus Methanol farblose Kristalle vom F.224 bis 225° bildet. Beispiel 3 7o Teile ß-Naphthvlamin werden in iooo Teilen Toluol gelöst und unter Rühren bei 8o° mit 7oTeilen y-Chlorbuttersäureclilorid versetzt. Nachdem das Reaktionsgemisch 2 bis 3 Stunden zum Sieden erhitzt wurde, wird auf 4o2 abgekühlt. Dann läßt man 5oo Teile 2oo/oige Natronlauge zufließen und rührt 2 Stunden weiter, bis klare Lösung erfolgt ist. Man trennt das Toluol ab, klärt die wäßrige Schicht mit Tierkohle und säuert sie dann an, -,wobei das N-(ß-Naphtliyl)-a-pyrrolidon ausfällt. Es ist nach dem Umkristallisieren aus Methanol ein weißes Kristallpulver vom F. 129 bis i30°. Die Ausbeute beträgt 6o Teile.Example 2 211 parts of the sodium salt of 2-oxy-4-aminobenzoic acid are suspended in 500 parts of benzene and mixed with 14 parts of γ-chlorobutyric acid chloride with stirring offset. The reaction mixture warms up to 70 °. It will be at that temperature Stirred for a further 2 hours. Then proceed as in example i and get 16o Parts of N- (4 -Carboxy-3'-oxy # 1) @lienyl) -a-liyrrolidone, (read after recrystallization Forms colorless crystals from methanol from 224 to 225 °. Example 3 70 parts of β-naphtha laminate are dissolved in 100 parts of toluene and mixed with 70 parts of y-chlorobutyric acid chloride while stirring at 80 ° offset. After the reaction mixture has been heated to boiling for 2 to 3 hours, is cooled to 4o2. Then 500 parts of 2oo% sodium hydroxide solution are allowed to flow in and stir for a further 2 hours until a clear solution is obtained. The toluene is separated off, clarifies the aqueous layer with animal charcoal and then acidifies it, -, with the N- (ß-naphthyl) -a-pyrrolidone fails. It is a white crystal powder after recrystallization from methanol from F. 129 to i30 °. The yield is 60 parts.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N-Aryla-pyrrolidonen, dadurch gekennzeichnet, daß man aromatische Aminoverbindungen mit y-Chlorbuttersäureclilorid umsetzt und die erhaltenen y-Clilorbuttersäurearylamide mit Alkali behandelt.PATENT CLAIM: Process for the production of N-aryla-pyrrolidones, characterized in that aromatic amino compounds with γ-chlorobutyric acid chloride and the y-Clilorbutyric acid arylamides obtained are treated with alkali.
DEB13140A 1950-12-22 1950-12-22 Process for the preparation of N-aryl-ª ‡ -pyrrolidones Expired DE850007C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB13140A DE850007C (en) 1950-12-22 1950-12-22 Process for the preparation of N-aryl-ª ‡ -pyrrolidones

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Application Number Priority Date Filing Date Title
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Publications (1)

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE935485C (en) * 1953-03-04 1955-11-24 Anorgana G M B H Process for the production of lactams
US4780545A (en) * 1985-09-24 1988-10-25 Lonza Ltd. Production of 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters
US4788294A (en) * 1986-06-19 1988-11-29 Lonza Ltd. Process for the production of 4-alkoxy-3-pyrrolin-2-ones
US4812578A (en) * 1986-06-26 1989-03-14 Lonza Ltd. Synthesis of tetramic acid
US4824966A (en) * 1985-09-24 1989-04-25 Lonza Ltd. Process for the production of 4-hydroxy-2-oxo-pyrrolidin-1-yl acetamide
US4843166A (en) * 1986-06-26 1989-06-27 Lonza Ltd. 4-benzyloxy-3-pyrrolin-2-on-1-yl acetamide production
US4876350A (en) * 1986-10-18 1989-10-24 Lonza Ltd. Process for the production of (+) biotin
US4906765A (en) * 1986-09-24 1990-03-06 Lonza Ltd. Process for the production of 4-alkoxy-2(5H) thiophenones
US5008402A (en) * 1988-09-06 1991-04-16 Lonza Ltd. Process for production of 5-alkyl tetramic acids
US5084578A (en) * 1989-03-15 1992-01-28 Lonza Ltd. Process for producing 1,3-substituted tetrahydro-1H-thieno-[3,4-D]-imidazol-2(3H)-on-4-ylidene pentanoic acid ester
US5093503A (en) * 1985-01-16 1992-03-03 Lonza Ltd. Process for the production of thiotetronic acid
US6242500B1 (en) 1996-12-06 2001-06-05 Amcol International Corporation Intercalates and exfoliates formed with long chain (C6+) or aromatic matrix polymer-compatible monomeric, oligomeric or polymeric intercalant compounds, and composite materials containing same

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE935485C (en) * 1953-03-04 1955-11-24 Anorgana G M B H Process for the production of lactams
US5093503A (en) * 1985-01-16 1992-03-03 Lonza Ltd. Process for the production of thiotetronic acid
US4780545A (en) * 1985-09-24 1988-10-25 Lonza Ltd. Production of 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters
US4824966A (en) * 1985-09-24 1989-04-25 Lonza Ltd. Process for the production of 4-hydroxy-2-oxo-pyrrolidin-1-yl acetamide
US4880940A (en) * 1985-09-24 1989-11-14 Lonza Ltd. 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters
US4788294A (en) * 1986-06-19 1988-11-29 Lonza Ltd. Process for the production of 4-alkoxy-3-pyrrolin-2-ones
US4879393A (en) * 1986-06-26 1989-11-07 Lonza Ltd. 4-Benzyloxy-3-pyrrolin-2-on-1-yl acetamide production
US4868314A (en) * 1986-06-26 1989-09-19 Lonza Ltd. 4-benzyloxy-3-pyrrolin-2-on-1-yl acetamide production
US4812578A (en) * 1986-06-26 1989-03-14 Lonza Ltd. Synthesis of tetramic acid
US4877884A (en) * 1986-06-26 1989-10-31 Lonza Ltd. 4-benzyloxy-3-pyrrolin-2-on-1-yl acetamide production
US4855451A (en) * 1986-06-26 1989-08-08 Lonza Ltd. 4-benzyloxy-3-pyrrolin-2-one, its production and use for synthesis of tetramic acid
US4843166A (en) * 1986-06-26 1989-06-27 Lonza Ltd. 4-benzyloxy-3-pyrrolin-2-on-1-yl acetamide production
US4906759A (en) * 1986-09-24 1990-03-06 Lonza Ltd. Process for the production of 4-alkoxy-2(5H) thiophenones
US4906765A (en) * 1986-09-24 1990-03-06 Lonza Ltd. Process for the production of 4-alkoxy-2(5H) thiophenones
US4931570A (en) * 1986-09-24 1990-06-05 Lonza Ltd. Process for the production of 4-alkoxy-2(5H) thiophenones
US4876350A (en) * 1986-10-18 1989-10-24 Lonza Ltd. Process for the production of (+) biotin
US5117003A (en) * 1986-12-18 1992-05-26 Lonza Ltd. Process for the production of (+) biotin
US5008402A (en) * 1988-09-06 1991-04-16 Lonza Ltd. Process for production of 5-alkyl tetramic acids
US5084578A (en) * 1989-03-15 1992-01-28 Lonza Ltd. Process for producing 1,3-substituted tetrahydro-1H-thieno-[3,4-D]-imidazol-2(3H)-on-4-ylidene pentanoic acid ester
US5086185A (en) * 1989-03-15 1992-02-04 Lonza Ltd. Process for producing 1,3-substituted tetrahydro-1H-thieno-[3,4-d]-imidazol-2(3H)-on-4-ylidene pentanoic acid ester
US6242500B1 (en) 1996-12-06 2001-06-05 Amcol International Corporation Intercalates and exfoliates formed with long chain (C6+) or aromatic matrix polymer-compatible monomeric, oligomeric or polymeric intercalant compounds, and composite materials containing same

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