NL8700656A - NEW METHOD. - Google Patents
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- NL8700656A NL8700656A NL8700656A NL8700656A NL8700656A NL 8700656 A NL8700656 A NL 8700656A NL 8700656 A NL8700656 A NL 8700656A NL 8700656 A NL8700656 A NL 8700656A NL 8700656 A NL8700656 A NL 8700656A
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- process according
- acetone
- methoxy
- naphthaldehyde
- takes place
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
Description
- 1 - *»· t -- 1 - * »t -
VV
Nieuwe werkwijze.New method.
Deze uitvinding betreft een nieuwe werkwijze voor het bereiden van een tussenprodukt voor de bereiding van 4-(6-methoxy-naftyl-2)butanon-2.This invention relates to a new process for preparing an intermediate for the preparation of 4- (6-methoxy-naphthyl-2) butanone-2.
Het Amerikaanse octrooischrift 4.061.779 beschrijft 5 4-(6-methoxynaftyl-2)butanon-2 (nabumeton) en het gebruik daar van bij de behandeling van rheuma en arthritis. Een aantal methoden voor de bereiding van deze verbinding zijn er ook beschreven.U.S. Patent 4,061,779 describes 4- (6-methoxynaphthyl-2) butanone-2 (nabumetone) and its use in the treatment of rheumatism and arthritis. A number of methods for the preparation of this compound have also been described.
De Amerikaanse octrooischriften 4.221.741 en 4.247.709 beschrijven nog andere werkwijzen voor het bereiden van nabumeton.U.S. Patents 4,221,741 and 4,247,709 describe still other methods of preparing nabumetone.
10 Nu is een werkwijze gevonden voor het bereiden van het B-ketol dat hierbij een tussenprodukt is, nuttig voor de bereiding van nabumeton. Deze werkwijze wordt gekenmerkt door de condensatie van 6-methoxy-B-naftaldehyd met aceton.A process has now been found for preparing the B-ketol which is an intermediate herein, useful for the preparation of nabumetone. This method is characterized by the condensation of 6-methoxy-B-naphthaldehyde with acetone.
Deze uitvinding verschaft dus een werkwijze voor het be-15 reiden'van het β-ketol volgens de formule van het formuleblad, die hieruit bestaat dat men 6-methoxy-B-naftaldehyd in aanwezigheid van een base bij verlaagde temperatuur met aceton laat reageren. Het B-ketol volgens formule 1 kan men dan door katalytische hydrogenering tot nabumeton hydrogeneren.The present invention thus provides a process for preparing the β-ketol according to the formula of the formula, which consists in reacting 6-methoxy-B-naphthaldehyde with acetone in the presence of a base at a reduced temperature. The B-ketol according to formula 1 can then be hydrogenated to nabumetone by catalytic hydrogenation.
20 Bij voorkeur gebeurt de condensatie van 6-methoxy-B-naftal- dehyd met aceton beneden 5°C. Bij hogere temperaturen, d.i. bij kamertemperatuur, is er toenemende neiging tot vorming van het overeenkomstige α,β-onverzadigde keton, zoals in voorbeeld 4 van het Britse octrooischrift 1.474.377 beschreven is.Preferably, the condensation of 6-methoxy-B-naphthaldehyde with acetone takes place below 5 ° C. At higher temperatures, i.e. at room temperature, there is an increasing tendency to form the corresponding α, β-unsaturated ketone, as described in Example 4 of British Patent 1,474,377.
25 De reactie gebeurt geschikt in waterig aceton met NaOHThe reaction is suitably carried out in aqueous acetone with NaOH
als base, en het produkt wordt met ether geëxtraheerd.as the base, and the product is extracted with ether.
In een bevoorkeurde uitvoeringsvorm worden de condensatie van 6-methoxy-B-naftaldehyd met aceton en de daarop volgende reductie gecombineerd tot een bereiding "in situ". De basische 30 oplossing van de verbinding volgens de formule wordt met zuur geneutraliseerd en de daarop aansluitende hydrogenering gebeurt zonder isoleren van het B-ketol.In a preferred embodiment, the condensation of 6-methoxy-B-naphthaldehyde with acetone and the subsequent reduction are combined into an "in situ" preparation. The basic solution of the compound of the formula is neutralized with acid and the subsequent hydrogenation is carried out without isolation of the B-ketol.
8700655 f - 2 - ιΛ, -¾8700655 f - 2 - ιΛ, -¾
De hydrogenering van de verbinding volgens de formule kan bij lage, middelmatige of hoge waterstofdrukken gebeuren, bijvoorbeeld bij 0,5 tot 4 atmosfeer waterstof, maar in het algemeen verdient een druk tussen 0,9 en 1,5 atmosfeer de voorkeur, bij-5 voorbeeld met 1 atmosfeer waterstof.The hydrogenation of the compound of the formula can be carried out at low, medium or high hydrogen pressures, for example at 0.5 to 4 atmospheres of hydrogen, but generally a pressure between 0.9 and 1.5 atmospheres is preferred, at -5 example with 1 atmosphere of hydrogen.
De hydrogenering zal in aanwezigheid van een katalysator gebeuren, bijvoorbeeld een edelmetaal zoals palladium, waarnaar de voorkeur uitgaat. Geschikte vormen van palladium-kataly-satoren zijn palladium-op-kool, palladium-op-bariumsulfaat en 10 palladium-op-calciumcarbonaat. Palladium-op-kool heeft de voorkeur.The hydrogenation will take place in the presence of a catalyst, for example a precious metal such as palladium, which is preferred. Suitable forms of palladium catalysts are palladium-on-carbon, palladium-on-barium sulfate and palladium-on-calcium carbonate. Palladium on charcoal is preferred.
Geschikte inerte oplosmiddelen voor de reactie zijn lagere alkoholen, zwakke zuren (zoals azijnzuur), esters, (zoals ethylacetaat), halogeenkoolwaterstoffen en ketonen zoals 4-methyl-15 pentanon-2 en aceton, en geschikte mengsels van twee of meer daarvan. Een mengsel van ethanol met ethylacetaat of van azijnzuur met aceton is bijzonder geschikt. De reactie kan ook in waterig medium plaats vinden.Suitable inert solvents for the reaction are lower alcohols, weak acids (such as acetic acid), esters (such as ethyl acetate), halohydrocarbons and ketones such as 4-methyl-15-pentanone-2 and acetone, and suitable mixtures of two or more thereof. A mixture of ethanol with ethyl acetate or of acetic acid with acetone is particularly suitable. The reaction can also take place in aqueous medium.
De reactie kan bij kamertemperatuur of daarboven plaats 20 vinden, bijvoorbeeld tussen 20° en 70°C, en nog beter tussen 40° en 60°C, bij voorkeur omstreeks 55°C.The reaction can take place at room temperature or above, for example between 20 ° and 70 ° C, and even better between 40 ° and 60 ° C, preferably around 55 ° C.
Als de reactie afgelopen is (bijvoorbeeld door DLC vast te stellen,4 of uit het ophouden van de waterstofopname) kan de gewenste verbinding verkregen worden door de katalysator af te 25 filtreren en het oplosmiddel te verwijderen, bijvoorbeeld door verdampen onder verlaagde druk.When the reaction is complete (for example, by determining TLC, or from cessation of hydrogen uptake), the desired compound can be obtained by filtering off the catalyst and removing the solvent, for example, by evaporation under reduced pressure.
Desgewenst kan de aldus verkregen verbinding door her-kristalliseren verder gezuiverd worden, bijvoorbeeld uit waterige ethanol.If desired, the compound thus obtained can be further purified by recrystallization, for example from aqueous ethanol.
30 De volgende voorbeelden lichten de uitvinding toe.The following examples illustrate the invention.
Voorbeeld IExample I
4-hydroxy-4-(6-methoxynafty1-2)butanon-24-hydroxy-4- (6-methoxynaphthyl-2) butanone-2
Een mengsel van 15,0 g 6-methoxy-f3-naftaldehyd en 150 ml aceton werd met een ij s-water-bad af gekoeld en 6,4 ml 2N NaOH in 35 water werd toegevoegd. Na 2j uur roeren in de koude werd de pHA mixture of 15.0 g of 6-methoxy-3-naphthaldehyde and 150 ml of acetone was cooled with an ice-water bath and 6.4 ml of 2N NaOH in water was added. After stirring for 2 hours in the cold, the pH became
met verdund zuur tot 8 verlaagd. De oplossing werd met 250 ml water 8700656 jü ^r.reduced to 8 with dilute acid. The solution was washed with 250 ml of water 8700656 µl.
' -3--3-
VV
en 500 ml ether geschud. De ether-laag werd met water gewassen, gedroogd en onder verlaagde druk gedestilleerd totdat een kristallijn neerslag van 4-hydroxy-4-(6-methoxynaftyl-2)butanon-2 begon te vormen (opbrengst 16,2 g met smp. 106-7°). Herkristalliseren 5 uit ethylacetaat gaf kleurloze naaldvormige kristallen met smp.and shaken 500 ml of ether. The ether layer was washed with water, dried and distilled under reduced pressure until a crystalline precipitate of 4-hydroxy-4- (6-methoxynaphthyl-2) butanone-2 started to yield (yield 16.2 g, mp 106-). 7 °). Recrystallization from ethyl acetate gave colorless acicular crystals with m.p.
107,5-8°.107.5-8 °.
IR-spectrum (muil): 1605, 1795 en 3450 cm ^. NMR (in CDCl^ bij 90 MHz): 2,15 (s, 3H), 2,9 (m, 2H), 3,4 (d, H), 3,85 (s, 3H), 5,25 (m, H) en 7,05-7,75 (m, 6H) dpm. Element-analyse: 10 C 73,5 Z, H 6,7 Z» berekend voor C25H^g°3» c 73,8 Z, H 6,6 Z.IR spectrum (mouth): 1605, 1795 and 3450 cm @ -1. NMR (in CDCl 3 @ 90 MHz): 2.15 (s, 3H), 2.9 (m, 2H), 3.4 (d, H), 3.85 (s, 3H), 5.25 ( m, H) and 7.05-7.75 (m, 6H) ppm. Elemental analysis: 10 C 73.5 Z, H 6.7 Z, calculated for C 25 H 15 g 3, c 73.8 Z, H 6.6 Z.
Voorbeeld IIExample II
4-(6-methoxynafty1-2)butanon-24- (6-methoxynaphthyl-2) butanone-2
Een oplossing van 3,66 g 4-hydroxy-4-(6-methoxynaftyl- 2)butanon-2 in 60 ml ethanol en 40 ml ethylacetaat werd een uur 15 lang onder een atmosfeer van waterstof hevig geschud terwijl het net aan de kook gehouden werd. Daarna werd de katalysator verwijderd en werd de oplossing bij verlaagde druk drooggedampt, wat een serie porties kristallijn produkt gaf, totale opbrengst 2,80 g.A solution of 3.66 g of 4-hydroxy-4- (6-methoxynaphthyl-2) butanone-2 in 60 ml of ethanol and 40 ml of ethyl acetate was shaken vigorously under an atmosphere of hydrogen for an hour while it was just boiling. became. The catalyst was then removed and the solution was evaporated to dryness under reduced pressure to give a batch of crystalline portions, total yield 2.80 g.
Met IR- en NMR-spectroscopie werd aangetoond dat dit 4-(6-methoxy-20 nafty1-2)butanon-2 was, met daarin een beetje onveranderde hydroxy-verbinding.IR and NMR spectroscopy showed this to be 4- (6-methoxy-20-naphthyl-2) -butanone-2, containing a little unchanged hydroxy compound.
Voorbeeld IIIExample III
Een oplossing van 156 mg 4-hydroxy-4-(6-methoxynaftyl-2)-butanon-2 in 2,0 ml aceton, 0,05 ml water en 1,0 ml azijnzuur werd 25 onder een atmosfeer van waterstof met 20 mg 10 Z palladium-op-kool geschud en onder tussen tot 55° verwarmd. Met tussenpozen werden monsters genomen en door HFLC vergeleken met een standaardmengsel van uitgangsstof (A), 2-hydroxy-4-(6-methoxynaftyl—2)-butaan (B) en 4-(6-methoxynaftyl-2)butanon-2 (C). Het gehalte van 30 het reactiemengsel aan (C) steeg tot een maximum van 94 Z, dat na 6 uur hydrogeneren bij 55° bereikt was. Op dat moment waren de gehalten aan (A) en (B) respectievelijk 3 % en 4 Z.A solution of 156 mg of 4-hydroxy-4- (6-methoxynaphthyl-2) -butanone-2 in 2.0 ml of acetone, 0.05 ml of water and 1.0 ml of acetic acid was made under an atmosphere of hydrogen with 20 mg Shake 10 Z palladium on charcoal and warm to 55 ° below. Samples were taken at intervals and compared by HFLC to a standard mixture of starting material (A), 2-hydroxy-4- (6-methoxynaphthyl-2) -butane (B) and 4- (6-methoxynaphthyl-2) butanone-2 ( C). The content of the reaction mixture of (C) rose to a maximum of 94 Z, which was reached after 55 hours of hydrogenation at 55 °. At that time, the levels of (A) and (B) were 3% and 4 Z, respectively.
Voorbeeld IVExample IV
4-(6-methoxynaftyl-2)-butanon-2 35 Een oplossing van 6,0 g 6-methoxy-f3-naftaldehyd in 100 ml aceton werd met een ijs-water-bad afgekoeld en 2,5 ml 6700658 - 4 - w· 2N NaOH in water werd toegevoegd. Na 2¾ uur roeren in de kou werden 50 ml azijnzuur en 1,0 g 10 %palladium-op-kool toegevoegd.4- (6-methoxynaphthyl-2) -butanone-2 35 A solution of 6.0 g of 6-methoxy-f3-naphthaldehyde in 100 ml of acetone was cooled with an ice-water bath and 2.5 ml of 6700658-4 2N NaOH in water was added. After stirring for 2 hours in the cold, 50 ml of acetic acid and 1.0 g of 10% palladium on charcoal were added.
//
De suspensie werd ongeveer 6 uur onder een atmosfeer van waterstof hevig bij 55°C geschud.The suspension was shaken vigorously at 55 ° C under an atmosphere of hydrogen for about 6 hours.
5 Toen de reductie voltooid was werd de katalysator ver wijderd en werd de oplossing met 200 ml water en 150 ml ether geschud. De waterlaag werd afgescheiden en opnieuw met 50 ml ether uitgetrokken. De ether-extracten werden bij elkaar gedaan, met overmaat NaHCO^-oplossing gewassen en op Na^SO^ gedroogd. Het op-10 losmiddel werd verwijderd en dit gaf een serie porties van het ruwe titelprodukt, in totaal 6,2 g.When the reduction was complete, the catalyst was removed and the solution was shaken with 200 ml of water and 150 ml of ether. The water layer was separated and extracted again with 50 ml of ether. The ether extracts were combined, washed with excess NaHCO 2 solution and dried over Na 2 SO 4. The solvent was removed to give a series of 6.2 g portions of the crude title product.
Na herkristalliseren uit heet ethanol had men 5,0 g 4-(6-methoxynaftyl-2)butanon-2 met smp. 81-83i°.After recrystallization from hot ethanol, 5.0 g of 4- (6-methoxynaphthyl-2) butanone-2 were obtained with m.p. 81-83i °.
15 870 0 65615 870 0 656
Claims (10)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB868607119A GB8607119D0 (en) | 1986-03-21 | 1986-03-21 | Process |
GB8607119 | 1986-03-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
NL8700656A true NL8700656A (en) | 1987-10-16 |
Family
ID=10595051
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL8700656A NL8700656A (en) | 1986-03-21 | 1987-03-20 | NEW METHOD. |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS62230744A (en) |
CH (1) | CH671014A5 (en) |
DK (1) | DK142387A (en) |
ES (1) | ES2004267A6 (en) |
GB (1) | GB8607119D0 (en) |
GR (1) | GR870454B (en) |
NL (1) | NL8700656A (en) |
SE (1) | SE8701168L (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5756851A (en) * | 1996-10-21 | 1998-05-26 | Albemarle Corporation | Production of nabumetone or precursors thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2242972A1 (en) * | 1973-09-11 | 1975-04-04 | Beecham Group Ltd | |
EP0003643A1 (en) * | 1978-01-27 | 1979-08-22 | Beecham Group Plc | Process for the preparation of 4-(6-methoxy-2-naphthyl)-butan-2-one; 4-(6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one and a process for its preparation |
-
1986
- 1986-03-21 GB GB868607119A patent/GB8607119D0/en active Pending
-
1987
- 1987-03-19 GR GR870454A patent/GR870454B/en unknown
- 1987-03-19 CH CH104887A patent/CH671014A5/en not_active IP Right Cessation
- 1987-03-19 DK DK142387A patent/DK142387A/en not_active Application Discontinuation
- 1987-03-20 NL NL8700656A patent/NL8700656A/en not_active Application Discontinuation
- 1987-03-20 ES ES8700790A patent/ES2004267A6/en not_active Expired
- 1987-03-20 SE SE8701168A patent/SE8701168L/en not_active Application Discontinuation
- 1987-03-20 JP JP6773787A patent/JPS62230744A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2242972A1 (en) * | 1973-09-11 | 1975-04-04 | Beecham Group Ltd | |
EP0003643A1 (en) * | 1978-01-27 | 1979-08-22 | Beecham Group Plc | Process for the preparation of 4-(6-methoxy-2-naphthyl)-butan-2-one; 4-(6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one and a process for its preparation |
Non-Patent Citations (4)
Title |
---|
CHEMICAL ABSTRACTS, vol. 090, no. 1, 1 January 1979, Columbus, Ohio, US; abstract no. 000223, GOUDIE A C ET AL: "4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds" * |
CHEMICAL ABSTRACTS, vol. 103, no. 17, 28 October 1985, Columbus, Ohio, US; abstract no. 141569, LIU K ET AL: "Synthesis of nabumetone" * |
J. MED. CHEM. (JMCMAR,00222623);78; VOL.21 (12); PP.1260-4, BEECHAM PHARM.;MED. RES. CENT.; HARLOW/ESSEX; ENGL. * |
YIYAO GONGYE (YIGODN);85; VOL.16 (4); PP.147-9, JIANGSU PHARM. IND. CO.;PEOP. REP. CHINA (CN) * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5756851A (en) * | 1996-10-21 | 1998-05-26 | Albemarle Corporation | Production of nabumetone or precursors thereof |
US5907069A (en) * | 1996-10-21 | 1999-05-25 | Albemarle Corporation | Production of nabumetone or precursors thereof |
Also Published As
Publication number | Publication date |
---|---|
DK142387A (en) | 1987-09-22 |
DK142387D0 (en) | 1987-03-19 |
JPS62230744A (en) | 1987-10-09 |
SE8701168L (en) | 1987-09-22 |
GB8607119D0 (en) | 1986-04-30 |
ES2004267A6 (en) | 1988-12-16 |
CH671014A5 (en) | 1989-07-31 |
GR870454B (en) | 1987-07-10 |
SE8701168D0 (en) | 1987-03-20 |
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