BG61317B2 - 3-(6'метокси-2'-нафтилметил)-2,4 пентандион,метод за получаването му и междинни съединения - Google Patents
3-(6'метокси-2'-нафтилметил)-2,4 пентандион,метод за получаването му и междинни съединения Download PDFInfo
- Publication number
- BG61317B2 BG61317B2 BG098346A BG9834693A BG61317B2 BG 61317 B2 BG61317 B2 BG 61317B2 BG 098346 A BG098346 A BG 098346A BG 9834693 A BG9834693 A BG 9834693A BG 61317 B2 BG61317 B2 BG 61317B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- formula
- compound
- methoxy
- preparation
- come
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- VZBLASFLFFMMCM-UHFFFAOYSA-N 6-methoxynaphthalene-2-carbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(OC)=CC=C21 VZBLASFLFFMMCM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000009833 condensation Methods 0.000 claims abstract description 6
- 230000005494 condensation Effects 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 230000006196 deacetylation Effects 0.000 claims abstract description 3
- 238000003381 deacetylation reaction Methods 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000005594 diketone group Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- -1 halogen hydrocarbon Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/12—Ketones containing more than one keto group
-
- 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
- C07C45/62—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 hydrogenation of carbon-to-carbon double or triple bonds
-
- 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
-
- 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
- C07C45/74—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 dehydration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Cleaning Or Drying Semiconductors (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878707200A GB8707200D0 (en) | 1987-03-26 | 1987-03-26 | Chemical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG61317B2 true BG61317B2 (bg) | 1997-05-30 |
Family
ID=10614672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG098346A BG61317B2 (bg) | 1987-03-26 | 1993-12-29 | 3-(6'метокси-2'-нафтилметил)-2,4 пентандион,метод за получаването му и междинни съединения |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0288144B1 (de) |
| JP (1) | JP2598296B2 (de) |
| KR (1) | KR960009161B1 (de) |
| AT (1) | ATE89257T1 (de) |
| AU (1) | AU612352B2 (de) |
| BG (1) | BG61317B2 (de) |
| CA (1) | CA1310333C (de) |
| DE (1) | DE3880880T2 (de) |
| DK (1) | DK172560B1 (de) |
| ES (1) | ES2056912T3 (de) |
| GB (1) | GB8707200D0 (de) |
| HK (1) | HK1004545A1 (de) |
| IE (1) | IE61580B1 (de) |
| NZ (1) | NZ224006A (de) |
| PT (1) | PT87069B (de) |
| ZA (1) | ZA882101B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5202495A (en) * | 1987-03-26 | 1993-04-13 | Callander Sidney E | Chemical process |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4910664B1 (de) * | 1969-07-21 | 1974-03-12 | ||
| US4061779A (en) * | 1973-09-11 | 1977-12-06 | Beecham Group Limited | Naphthalene derivatives having anti-inflammatory activity |
| AT343104B (de) * | 1975-01-08 | 1978-05-10 | Beecham Group Ltd | Verfahren zur herstellung von neuen naphthalinderivaten |
| GB1504442A (en) * | 1976-11-25 | 1978-03-22 | Beecham Group Ltd | Naphthyl derivatives |
| EP0011925B1 (de) * | 1978-11-23 | 1982-09-22 | Beecham Group Plc | Naphthalin-Derivate, Verfahren zu ihrer Herstellung und Verwendung in entzündungshemmenden pharmazeutischen Zusammensetzungen |
-
1987
- 1987-03-26 GB GB878707200A patent/GB8707200D0/en active Pending
-
1988
- 1988-03-16 DE DE88302285T patent/DE3880880T2/de not_active Expired - Fee Related
- 1988-03-16 EP EP88302285A patent/EP0288144B1/de not_active Expired - Lifetime
- 1988-03-16 ES ES88302285T patent/ES2056912T3/es not_active Expired - Lifetime
- 1988-03-16 AT AT88302285T patent/ATE89257T1/de not_active IP Right Cessation
- 1988-03-24 PT PT87069A patent/PT87069B/pt not_active IP Right Cessation
- 1988-03-24 ZA ZA882101A patent/ZA882101B/xx unknown
- 1988-03-24 DK DK198801621A patent/DK172560B1/da not_active IP Right Cessation
- 1988-03-24 NZ NZ224006A patent/NZ224006A/en unknown
- 1988-03-24 AU AU13704/88A patent/AU612352B2/en not_active Ceased
- 1988-03-24 CA CA000562375A patent/CA1310333C/en not_active Expired - Fee Related
- 1988-03-24 IE IE89288A patent/IE61580B1/en not_active IP Right Cessation
- 1988-03-25 KR KR1019880003253A patent/KR960009161B1/ko not_active IP Right Cessation
- 1988-03-25 JP JP63071699A patent/JP2598296B2/ja not_active Expired - Fee Related
-
1993
- 1993-12-29 BG BG098346A patent/BG61317B2/bg unknown
-
1998
- 1998-04-28 HK HK98103615A patent/HK1004545A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2056912T3 (es) | 1994-10-16 |
| PT87069B (pt) | 1992-07-31 |
| ZA882101B (en) | 1989-09-27 |
| DE3880880T2 (de) | 1993-10-07 |
| AU1370488A (en) | 1988-09-29 |
| GB8707200D0 (en) | 1987-04-29 |
| JPS63255243A (ja) | 1988-10-21 |
| JP2598296B2 (ja) | 1997-04-09 |
| PT87069A (pt) | 1988-04-01 |
| KR880011062A (ko) | 1988-10-26 |
| ATE89257T1 (de) | 1993-05-15 |
| EP0288144A2 (de) | 1988-10-26 |
| DK162188A (da) | 1988-09-27 |
| EP0288144B1 (de) | 1993-05-12 |
| KR960009161B1 (ko) | 1996-07-16 |
| DE3880880D1 (de) | 1993-06-17 |
| NZ224006A (en) | 1991-05-28 |
| DK162188D0 (da) | 1988-03-24 |
| IE880892L (en) | 1988-09-26 |
| EP0288144A3 (en) | 1990-02-14 |
| AU612352B2 (en) | 1991-07-11 |
| DK172560B1 (da) | 1999-01-18 |
| HK1004545A1 (en) | 1998-11-27 |
| IE61580B1 (en) | 1994-11-16 |
| CA1310333C (en) | 1992-11-17 |
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