NO327046B1 - Fremgangsmate for fremstilling av 3-(hydroksymetyl)kromen-4-oner - Google Patents
Fremgangsmate for fremstilling av 3-(hydroksymetyl)kromen-4-oner Download PDFInfo
- Publication number
- NO327046B1 NO327046B1 NO20011401A NO20011401A NO327046B1 NO 327046 B1 NO327046 B1 NO 327046B1 NO 20011401 A NO20011401 A NO 20011401A NO 20011401 A NO20011401 A NO 20011401A NO 327046 B1 NO327046 B1 NO 327046B1
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- hydroxymethyl
- compounds
- halogen
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- CCUIZOSFSPCGLS-UHFFFAOYSA-N 3-(hydroxymethyl)chromen-4-one Chemical compound C1=CC=C2C(=O)C(CO)=COC2=C1 CCUIZOSFSPCGLS-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 230000018044 dehydration Effects 0.000 claims abstract description 3
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- 239000002535 acidifier Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 3
- OWBBAPRUYLEWRR-UHFFFAOYSA-N 4-hydroxycoumarin Chemical class C1=CC=C2OC(O)=CC(=O)C2=C1 OWBBAPRUYLEWRR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GDRIETDFLSQGKG-UHFFFAOYSA-N 1-phenyl-2-sulfinylethanone Chemical class O=S=CC(=O)C1=CC=CC=C1 GDRIETDFLSQGKG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FSMYWBQIMDSGQP-UHFFFAOYSA-N 4-oxochromene-3-carbaldehyde Chemical class C1=CC=C2C(=O)C(C=O)=COC2=C1 FSMYWBQIMDSGQP-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- -1 sodium acetate Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009801970A ES2154176B1 (es) | 1998-09-21 | 1998-09-21 | Nuevo procedimiento de obtencion de 3-(hidroximetil)cromen-4-onas. |
| PCT/EP1999/006946 WO2000017183A1 (fr) | 1998-09-21 | 1999-09-20 | 3-(hydroxymethyl)chromen-4-ones et mode d'elaboration |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20011401L NO20011401L (no) | 2001-03-20 |
| NO20011401D0 NO20011401D0 (no) | 2001-03-20 |
| NO327046B1 true NO327046B1 (no) | 2009-04-14 |
Family
ID=8305211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20011401A NO327046B1 (no) | 1998-09-21 | 2001-03-20 | Fremgangsmate for fremstilling av 3-(hydroksymetyl)kromen-4-oner |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6348605B1 (fr) |
| EP (1) | EP1115717B1 (fr) |
| JP (1) | JP3983979B2 (fr) |
| KR (1) | KR100547939B1 (fr) |
| AR (1) | AR017003A1 (fr) |
| AT (1) | ATE261437T1 (fr) |
| AU (1) | AU754043B2 (fr) |
| BR (1) | BR9914009B1 (fr) |
| CA (1) | CA2344664C (fr) |
| DE (1) | DE69915498T2 (fr) |
| DK (1) | DK1115717T3 (fr) |
| ES (1) | ES2154176B1 (fr) |
| IL (1) | IL141751A (fr) |
| NO (1) | NO327046B1 (fr) |
| NZ (1) | NZ510309A (fr) |
| PT (1) | PT1115717E (fr) |
| TW (1) | TW480254B (fr) |
| WO (1) | WO2000017183A1 (fr) |
| ZA (1) | ZA995877B (fr) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2378573A (en) * | 1939-07-08 | 1945-06-19 | Natta Giulio | Process for the manufacture of keto-alcohols |
| US3887584A (en) * | 1972-11-24 | 1975-06-03 | Warner Lambert Co | 3-(Hydroxymethyl)chromones |
| ES2101620B1 (es) * | 1994-03-18 | 1998-04-01 | Ferrer Int | Nuevo compuesto derivado del cromeno. |
| IL112764A0 (en) | 1994-03-18 | 1995-05-26 | Ferrer Int | New chromene derivatives |
| ES2101646B1 (es) * | 1995-04-12 | 1998-04-01 | Ferrer Int | Nuevo compuesto derivado del cromeno. |
-
1998
- 1998-09-21 ES ES009801970A patent/ES2154176B1/es not_active Expired - Fee Related
-
1999
- 1999-09-10 TW TW088115637A patent/TW480254B/zh not_active IP Right Cessation
- 1999-09-13 AR ARP990104580A patent/AR017003A1/es active IP Right Grant
- 1999-09-13 ZA ZA9905877A patent/ZA995877B/xx unknown
- 1999-09-20 DE DE69915498T patent/DE69915498T2/de not_active Expired - Lifetime
- 1999-09-20 EP EP99953745A patent/EP1115717B1/fr not_active Expired - Lifetime
- 1999-09-20 CA CA002344664A patent/CA2344664C/fr not_active Expired - Fee Related
- 1999-09-20 NZ NZ510309A patent/NZ510309A/en not_active IP Right Cessation
- 1999-09-20 US US09/787,113 patent/US6348605B1/en not_active Expired - Fee Related
- 1999-09-20 KR KR1020017003562A patent/KR100547939B1/ko not_active IP Right Cessation
- 1999-09-20 DK DK99953745T patent/DK1115717T3/da active
- 1999-09-20 WO PCT/EP1999/006946 patent/WO2000017183A1/fr active IP Right Grant
- 1999-09-20 IL IL14175199A patent/IL141751A/xx not_active IP Right Cessation
- 1999-09-20 AU AU10331/00A patent/AU754043B2/en not_active Ceased
- 1999-09-20 PT PT99953745T patent/PT1115717E/pt unknown
- 1999-09-20 AT AT99953745T patent/ATE261437T1/de active
- 1999-09-20 BR BRPI9914009-8A patent/BR9914009B1/pt not_active IP Right Cessation
- 1999-09-20 JP JP2000574093A patent/JP3983979B2/ja not_active Expired - Fee Related
-
2001
- 2001-03-20 NO NO20011401A patent/NO327046B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100547939B1 (ko) | 2006-02-02 |
| NO20011401L (no) | 2001-03-20 |
| CA2344664C (fr) | 2006-11-07 |
| PT1115717E (pt) | 2004-07-30 |
| TW480254B (en) | 2002-03-21 |
| EP1115717A1 (fr) | 2001-07-18 |
| IL141751A0 (en) | 2002-03-10 |
| AR017003A1 (es) | 2001-08-22 |
| KR20010075229A (ko) | 2001-08-09 |
| DE69915498D1 (de) | 2004-04-15 |
| WO2000017183A1 (fr) | 2000-03-30 |
| JP2002526487A (ja) | 2002-08-20 |
| ATE261437T1 (de) | 2004-03-15 |
| AU754043B2 (en) | 2002-10-31 |
| NZ510309A (en) | 2002-06-28 |
| IL141751A (en) | 2005-03-20 |
| AU1033100A (en) | 2000-04-10 |
| BR9914009B1 (pt) | 2010-02-09 |
| DE69915498T2 (de) | 2004-08-19 |
| JP3983979B2 (ja) | 2007-09-26 |
| ES2154176B1 (es) | 2001-10-16 |
| BR9914009A (pt) | 2001-07-03 |
| ES2154176A1 (es) | 2001-03-16 |
| EP1115717B1 (fr) | 2004-03-10 |
| US6348605B1 (en) | 2002-02-19 |
| DK1115717T3 (da) | 2004-07-12 |
| NO20011401D0 (no) | 2001-03-20 |
| CA2344664A1 (fr) | 2000-03-30 |
| ZA995877B (en) | 2001-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |