DE376516T1 - Verfahren zur herstellung von nabumeton. - Google Patents
Verfahren zur herstellung von nabumeton.Info
- Publication number
- DE376516T1 DE376516T1 DE198989312781T DE89312781T DE376516T1 DE 376516 T1 DE376516 T1 DE 376516T1 DE 198989312781 T DE198989312781 T DE 198989312781T DE 89312781 T DE89312781 T DE 89312781T DE 376516 T1 DE376516 T1 DE 376516T1
- Authority
- DE
- Germany
- Prior art keywords
- process according
- catalyst
- nabumetone
- producing
- triphenylphosphine
- 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.)
- Pending
Links
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 title claims abstract 3
- 229960004270 nabumetone Drugs 0.000 title claims abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract 9
- 239000003054 catalyst Substances 0.000 claims abstract 5
- MKUWVMRNQOOSAT-UHFFFAOYSA-N methylvinylmethanol Natural products CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 claims abstract 4
- AYFJBMBVXWNYLT-UHFFFAOYSA-N 2-bromo-6-methoxynaphthalene Chemical compound C1=C(Br)C=CC2=CC(OC)=CC=C21 AYFJBMBVXWNYLT-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical group Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 150000002941 palladium compounds Chemical class 0.000 claims 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
Classifications
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Semiconductor Lasers (AREA)
- Developing Agents For Electrophotography (AREA)
Claims (8)
1. Verfahren zur Herstellung von Nabumetone, bei dem 2-Brom-6-methoxynaphthalin
mit 3-Buten-2-ol in Gegenwart eines Katalysators umgesetzt wird.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß der Katalysator eine Palladiumverbindung in Kombination
mit einem Liganden enthält, der dreiwertigen Phosphor enthält.
3. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß der Katalysator Palladium(II)-acetat ist in Kombination
mit Triphenylphosphin.
4. Verfahren nach Anspruch 2, dadurch gekennzeichnet,
daß der Katalysator ein Bis(triphenylphosphin)dichlorpalladium(II)-Komplex
ist.
5. Verfahren nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß die Reaktionstemperatur im Bereich von
120 °C bis 150 "C liegt.
6. Verfahren nach einem der Ansprüche 1 bis 5, dadurch
gekennzeichnet, daß die Reaktionszeit im Bereich von 0,25 bis 10 Stunden liegt.
7. Verfahren nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, daß die Reaktion in Gegenwart eines Lösungsmittels
durchgeführt wird.
8. Verfahren nach Anspruch 7, dadurch gekennzeichnet, daß das Lösungsmittel N-Methy!pyrrolidon ist.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28270988A | 1988-12-08 | 1988-12-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE376516T1 true DE376516T1 (de) | 1991-03-21 |
Family
ID=23082783
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE198989312781T Pending DE376516T1 (de) | 1988-12-08 | 1989-12-07 | Verfahren zur herstellung von nabumeton. |
DE8989312781T Expired - Fee Related DE68904888T2 (de) | 1988-12-08 | 1989-12-07 | Verfahren zur herstellung von nabumeton. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE8989312781T Expired - Fee Related DE68904888T2 (de) | 1988-12-08 | 1989-12-07 | Verfahren zur herstellung von nabumeton. |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0376516B1 (de) |
JP (1) | JPH02231446A (de) |
AT (1) | ATE85600T1 (de) |
CA (1) | CA2004042C (de) |
DE (2) | DE376516T1 (de) |
GR (2) | GR910300056T1 (de) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1223157A1 (de) * | 1995-06-07 | 2002-07-17 | Hoechst Celanese Corporation | Verwendung von 4-substituierten 2-butanonen zur Herstellung von Nabumetone |
US5600009A (en) * | 1996-04-09 | 1997-02-04 | Hoechst Celanese Corporation | Use of 4-substituted 2-butanones to prepare nabumetone |
IT1283638B1 (it) * | 1996-07-29 | 1998-04-23 | Archimica Spa | Procedimento per la preparazione di un naftilbutanone |
US5756851A (en) * | 1996-10-21 | 1998-05-26 | Albemarle Corporation | Production of nabumetone or precursors thereof |
AU5656698A (en) * | 1996-12-03 | 1998-06-29 | Recordati S.A. Chemical And Pharmaceutical Company | A process for the preparation of nabumetone |
US5741938A (en) * | 1997-02-21 | 1998-04-21 | Albemarle Corporation | Production of alkyl aralkyl keones from allylic-aralkenyl secondary alcohols |
US5847225A (en) * | 1997-04-25 | 1998-12-08 | Albemarle Corporation | Production of naphthyl-substituted ketones from naphthaldehydes |
US5861538A (en) * | 1997-08-04 | 1999-01-19 | Albemarle Corporation | Production of alkoxynaphthyl-substituted ketones from naphthaldehydes |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3922299A (en) * | 1974-03-05 | 1975-11-25 | Univ Delaware | Vinylic substitution reactions |
GB1476721A (en) * | 1974-08-20 | 1977-06-16 | Beecham Group Ltd | 4-6-methoxy-2-naphthyl-butan-2-one |
US4070374A (en) * | 1975-06-16 | 1978-01-24 | Givaudan Corporation | Process for the preparation of aryl substituted aldehydes, ketones and alcohols |
NL8803088A (nl) * | 1987-12-19 | 1989-07-17 | Beecham Group Plc | Werkwijze voor de bereiding van een butanonderivaat. |
-
1989
- 1989-11-28 CA CA002004042A patent/CA2004042C/en not_active Expired - Fee Related
- 1989-12-06 JP JP1317407A patent/JPH02231446A/ja active Pending
- 1989-12-07 AT AT89312781T patent/ATE85600T1/de not_active IP Right Cessation
- 1989-12-07 DE DE198989312781T patent/DE376516T1/de active Pending
- 1989-12-07 EP EP89312781A patent/EP0376516B1/de not_active Expired - Lifetime
- 1989-12-07 DE DE8989312781T patent/DE68904888T2/de not_active Expired - Fee Related
-
1991
- 1991-11-15 GR GR91300056T patent/GR910300056T1/el unknown
-
1993
- 1993-02-11 GR GR910400018T patent/GR3010337T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
CA2004042C (en) | 1999-11-02 |
EP0376516A1 (de) | 1990-07-04 |
EP0376516B1 (de) | 1993-02-10 |
JPH02231446A (ja) | 1990-09-13 |
GR3010337T3 (de) | 1994-04-29 |
DE68904888T2 (de) | 1993-05-27 |
CA2004042A1 (en) | 1990-06-08 |
DE68904888D1 (de) | 1993-03-25 |
GR910300056T1 (en) | 1991-11-15 |
ATE85600T1 (de) | 1993-02-15 |
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