NL1006654C2 - Preparation of 3-Methoxymethyl-quinoline - Google Patents

Preparation of 3-Methoxymethyl-quinoline Download PDF

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Publication number
NL1006654C2
NL1006654C2 NL1006654A NL1006654A NL1006654C2 NL 1006654 C2 NL1006654 C2 NL 1006654C2 NL 1006654 A NL1006654 A NL 1006654A NL 1006654 A NL1006654 A NL 1006654A NL 1006654 C2 NL1006654 C2 NL 1006654C2
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NL
Netherlands
Prior art keywords
preparation
alkali metal
methylquinoline
chloromethylquinoline
photochlorination
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Application number
NL1006654A
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Dutch (nl)
Inventor
Dirk Armand Wim Stanssens
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Dsm Nv
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Publication date
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Priority to NL1006654A priority Critical patent/NL1006654C2/en
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Publication of NL1006654C2 publication Critical patent/NL1006654C2/en

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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Quinoline Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Preparation of a 3-methoxymethylquinoline comprises photochlorinating the corresponding 3-methylquinoline and contacting the resulting 3-chloromethylquinoline with \- 1 equivalent of alkali metal methoxide.

Description

- 1 - PN 9331- 1 - PN 9331

WERKWIJZE VOOR DE BEREIDING VANMETHOD FOR PREPARING

3-METHOXYMETHYLCHINOLINE EN DERIVATEN DAARVAN 53-METHOXYMETHYLCHINOLINE AND ITS DERIVATIVES 5

De uitvinding betreft een nieuwe eenvoudige route voor de bereiding van een 3-methoxymethylchinoline waarin het overeenkomstige 3-methylchinoline via 10 fotochlorering wordt omgezet in het overeenkomstige 3-chloormethylchinoline en vervolgens het verkregen 3-chloormethylchinoline in contact wordt gebracht met ten minste 1,0 equivalent alkalimetaalmethanolaat.The invention relates to a new simple route for the preparation of a 3-methoxymethylquinoline in which the corresponding 3-methylquinoline is converted via photochlorination into the corresponding 3-chloromethylquinoline and then the resulting 3-chloromethylquinoline is contacted with at least 1.0 equivalent alkali metal methanolate.

3-Methoxymethylchinoline kan via oxidatie, 15 bijvoorbeeld via ozonolyse, worden omgezet in 5- methoxymethylpyridine-2,3-dicarbonzuur dat bijvoorbeeld wordt toegepast in de bereiding van herbicides van de klasse imidazolinonen.3-Methoxymethylquinoline can be converted via oxidation, for example via ozonolysis, into 5-methoxymethylpyridine-2,3-dicarboxylic acid, which is used, for example, in the preparation of herbicides of the class imidazolinones.

Bij de fotochlorering wordt een chloor-20 verbinding, in het bijzonder chloorgas, overgeleid, eventueel in combinatie met N2, onder straling, in het bijzonder UV-straling, bijvoorbeeld met behulp van een kwiklamp. De fotochlorering kan zowel in de vloeistoffase als in de gasfase worden uitgevoerd. De temperatuur 25 waarbij de fotochlorering wordt uitgevoerd is niet bijzonder kritisch en ligt in de praktijk veelal tussen 50 en 250°C, bij voorkeur tussen 70 en 200°C. De duur van de fotochlorering kan binnen wijde grenzen variëren en ligt typisch tussen 0,5 en 10 uur. Bij voorkeur wordt de 30 fotochlorering gedurende een zodanige tijd en bij een zodanige temperatuur uitgevoerd dat een conversie van 10-35%, in het bijzonder tussen 15 en 25% wordt bereikt. De vakman kan gemakkelijk de voor zijn specifieke situatie optimale combinatie van tijd en temperatuur bepalen.In photochlorination, a chlorine-20 compound, in particular chlorine gas, is passed, optionally in combination with N2, under radiation, in particular UV radiation, for example with the aid of a mercury lamp. The photochlorination can be carried out in both the liquid phase and the gas phase. The temperature at which the photochlorination is carried out is not particularly critical and in practice often lies between 50 and 250 ° C, preferably between 70 and 200 ° C. The duration of photochlorination can vary within wide limits and is typically between 0.5 and 10 hours. Preferably, the photochlorination is carried out for such a time and at such a temperature that a conversion of 10-35%, in particular between 15 and 25%, is achieved. The skilled person can easily determine the optimal combination of time and temperature for his specific situation.

35 Desgewenst kunnen additieven worden toegevoegd om eventuele ringchlorering te minimaliseren.If desired, additives can be added to minimize any ring chlorination.

1006654 - 2 -1006654 - 2 -

De omzetting van het verkregen 3-chloor-methylchinoline in het overeenkomstige 3-methoxymethyl-chinoline wordt uitgevoerd in aanwezigheid van tenminste 1 equivalente hoeveelheid alkalimetaal-methanolaat. Bij 5 voorkeur wordt 1,0-2,5 equivalent alkalimetaalmethanolaat toegepast. Het gebruiken van grotere hoeveelheden alkalimetaalmethanolaat is wel mogelijk, maar biedt in de praktijk geen voordeel. De omzetting met behulp van het alkali- metaalmethanolaat wordt bij voorkeur uitgevoerd 10 bij verhoogde temperatuur tussen 50 en 150°C. Bij voorkeur wordt als alkalimetaalmethanolaat natriummethanolaat toegepast.The conversion of the obtained 3-chloromethylquinoline to the corresponding 3-methoxymethylquinoline is carried out in the presence of at least 1 equivalent amount of alkali metal methanolate. Preferably 1.0-2.5 equivalent of alkali metal methanolate is used. The use of larger amounts of alkali metal methanolate is possible, but does not offer any advantage in practice. The reaction using the alkali metal methoxide is preferably carried out at an elevated temperature between 50 and 150 ° C. Sodium methanolate is preferably used as the alkali metal methanolate.

De bereiding van 5-methylchinoline is bekend en wordt bijvoorbeeld beschreven in Claret, Osborne, Chem.The preparation of 5-methylquinoline is known and is described, for example, in Claret, Osborne, Chem.

15 Ind. (London) 1970, 401.15 Ind. (London) 1970, 401.

10066541006654

Claims (6)

1. Werkwijze voor de bereiding van een 3-methoxy- 5 methylchinoline waarin het overeenkomstige 3- methylchinoline via fotochlorering wordt omgezet in het overeenkomstige 3-chloormethylchinoline en vervolgens het verkregen 5-chloormethylchinoline in contact wordt gebracht met ten minste 1,0 equivalent 10 alkalimetaalmethanolaat.A process for the preparation of a 3-methoxy-methylquinoline in which the corresponding 3-methylquinoline is photochlorinated to the corresponding 3-chloromethylquinoline and then the resulting 5-chloromethylquinoline is contacted with at least 1.0 equivalent of 10 alkali metal methanolate . 2. Werkwijze volgens conclusie 1 waarin als alkalimetaalmethanolaat natriummethanolaat wordt toegepast.2. Process according to claim 1, wherein sodium alkoxide is used as the alkali metal methanolate. 3. Werkwijze volgens conclusie 1 of 2 waarin 1,0-2,5 equivalent alkalimetaalmethanolaat wordt toegepast.The method according to claim 1 or 2, wherein 1.0-2.5 equivalent of alkali metal methanolate is used. 4. Werkwijze volgens een der conclusies 1-3, waarin de conversie bij de fotochlorering gekozen wordt tussen 10 en 35%.A method according to any one of claims 1-3, wherein the conversion in photochlorination is selected between 10 and 35%. 5. Werkwijze volgens een der conclusies 1-4, waarin het verkregen 3-methoxymethylchinoline vervolgens wordt 20 geoxideerd tot het overeenkomstige 5- methoxymethylpyr idine-2,3-dicarbonzuur.5. Process according to any one of claims 1-4, wherein the obtained 3-methoxymethylquinoline is subsequently oxidized to the corresponding 5-methoxymethylpyridine-2,3-dicarboxylic acid. 6. Werkwijze voor de bereiding van 5-methoxy-methylchinoline zoals beschreven en toegelicht aan de hand van de voorbeelden. 25 10066546. Process for the preparation of 5-methoxy-methylquinoline as described and illustrated by the examples. 25 1006654
NL1006654A 1997-07-24 1997-07-24 Preparation of 3-Methoxymethyl-quinoline NL1006654C2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
NL1006654A NL1006654C2 (en) 1997-07-24 1997-07-24 Preparation of 3-Methoxymethyl-quinoline

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL1006654 1997-07-24
NL1006654A NL1006654C2 (en) 1997-07-24 1997-07-24 Preparation of 3-Methoxymethyl-quinoline

Publications (1)

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NL1006654C2 true NL1006654C2 (en) 1999-01-26

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT407394B (en) * 1999-05-10 2001-02-26 Dsm Fine Chem Austria Gmbh METHOD FOR PRODUCING 2,3-PYRIDINE DICARBONIC ACIDS

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1246737B (en) * 1960-11-03 1967-08-10 Ici Ltd Process for the preparation of 2-beta-methoxyaethylpyridine
US4046656A (en) * 1976-12-06 1977-09-06 The Dow Chemical Company Photochlorination process for methyl aromatic compounds
EP0391696A2 (en) * 1989-04-07 1990-10-10 MITSUI TOATSU CHEMICALS, Inc. Process for preparing aromatic compounds having chlorinated side chains and method for stabilizing monochloro-side chain aromatic compounds
EP0609153A1 (en) * 1993-01-28 1994-08-03 Elf Atochem S.A. Photochemical gas/liquid process for the halogenation of alkylbenzenes
EP0612707A1 (en) * 1993-02-24 1994-08-31 ENICHEM SYNTHESIS S.p.A. Procedure for the photochlorination of alkyl-aromatic compounds

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1246737B (en) * 1960-11-03 1967-08-10 Ici Ltd Process for the preparation of 2-beta-methoxyaethylpyridine
US4046656A (en) * 1976-12-06 1977-09-06 The Dow Chemical Company Photochlorination process for methyl aromatic compounds
EP0391696A2 (en) * 1989-04-07 1990-10-10 MITSUI TOATSU CHEMICALS, Inc. Process for preparing aromatic compounds having chlorinated side chains and method for stabilizing monochloro-side chain aromatic compounds
EP0609153A1 (en) * 1993-01-28 1994-08-03 Elf Atochem S.A. Photochemical gas/liquid process for the halogenation of alkylbenzenes
EP0612707A1 (en) * 1993-02-24 1994-08-31 ENICHEM SYNTHESIS S.p.A. Procedure for the photochlorination of alkyl-aromatic compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT407394B (en) * 1999-05-10 2001-02-26 Dsm Fine Chem Austria Gmbh METHOD FOR PRODUCING 2,3-PYRIDINE DICARBONIC ACIDS

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