ATE148T1 - PROCESS FOR THE PREPARATION OF 2,3-DIHYDRO-2-AETHYLBENZOFURAN-5-YLEACETIC ACID. - Google Patents
PROCESS FOR THE PREPARATION OF 2,3-DIHYDRO-2-AETHYLBENZOFURAN-5-YLEACETIC ACID.Info
- Publication number
- ATE148T1 ATE148T1 AT79103127T AT79103127T ATE148T1 AT E148 T1 ATE148 T1 AT E148T1 AT 79103127 T AT79103127 T AT 79103127T AT 79103127 T AT79103127 T AT 79103127T AT E148 T1 ATE148 T1 AT E148T1
- Authority
- AT
- Austria
- Prior art keywords
- dihydro
- ethylbenzofurane
- acid
- solvent
- reaction
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 2
- 239000002904 solvent Substances 0.000 abstract 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 2
- PCYKOMNKTKPEET-UHFFFAOYSA-N 2-ethyl-2,3-dihydro-1-benzofuran Chemical compound C1=CC=C2OC(CC)CC2=C1 PCYKOMNKTKPEET-UHFFFAOYSA-N 0.000 abstract 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 2
- -1 aliphatic chlorinated hydrocarbons Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- OWZFULPEVHKEKS-UHFFFAOYSA-N ethyl 2-chloro-2-oxoacetate Chemical compound CCOC(=O)C(Cl)=O OWZFULPEVHKEKS-UHFFFAOYSA-N 0.000 abstract 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 2
- MYQXHLQMZLTSDB-UHFFFAOYSA-N 2-(2-ethyl-2,3-dihydro-1-benzofuran-5-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2OC(CC)CC2=C1 MYQXHLQMZLTSDB-UHFFFAOYSA-N 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- XSTQBSRXKNGBRF-UHFFFAOYSA-N ethyl 2-(2-ethyl-2,3-dihydro-1-benzofuran-5-yl)-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CC=C2OC(CC)CC2=C1 XSTQBSRXKNGBRF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003827 glycol group Chemical group 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1. A process for preparing 2,3-dihydro-2-ethylbenzofurane-5-ylacetic acid by reacting essentially equimolar quantities of chloroglyoxylic acid ethylester and 2,3-dihydro-2-ethylbenzofurane in the presence of a Friedel-Crafts catalyst in a solvent at low temperature as well as in the further course making use of a reaction with hydrazine hydrate as reactant, characterized in that one uses for the reaction of the chloroglyoxylic acid ethylester with the 2,3-dihydro-2-ethylbenzofurane as Friedel-Crafts catalyst titanium tetrachloride and/or tin tetrachloride an as a solvent 1 or more lower aliphatic chlorinated hydrocarbons and one applies as temperature form -30 to +50 degrees C as well as one makes to react the obtained 2,3-dihydro-2-ethylbenzofurane-5-ylglyoxylic acid ethylester isolated from the reaction mixture immediately with 80 to 100 % hydrazine hydrate in the presence of 1 or more alcohols having from 1 to 6 carbon atoms and/or glycoles having from 2 to 4 carbon atoms as solvent(s) to yield 2,3-dihydro-2-ethylbenzofurane-5-ylgyoxylic acid hydrazine hydrazone and one heats the latter immediately in the presence of a solution of 1 or more strong inorganic bases to a temperature of 100 to 200 degrees C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT03520/78A IT1111639B (en) | 1978-09-05 | 1978-09-05 | ACID PREPARATION PROCEDURE 2.3 DIHYDRO 2 ETHYL BENZOFURAN 5 IL ACETICO |
| EP79103127A EP0008752B1 (en) | 1978-09-05 | 1979-08-24 | Process for the preparation of 2,3-dihydro-2-ethyl-benzofuran-5-acetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE148T1 true ATE148T1 (en) | 1981-09-15 |
Family
ID=11108924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT79103127T ATE148T1 (en) | 1978-09-05 | 1979-08-24 | PROCESS FOR THE PREPARATION OF 2,3-DIHYDRO-2-AETHYLBENZOFURAN-5-YLEACETIC ACID. |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0008752B1 (en) |
| AT (1) | ATE148T1 (en) |
| DE (1) | DE2960637D1 (en) |
| DK (1) | DK369479A (en) |
| ES (1) | ES483856A1 (en) |
| IT (1) | IT1111639B (en) |
| NO (1) | NO792850L (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0026593A1 (en) * | 1979-09-15 | 1981-04-08 | Pfizer Limited | Bicyclic keto- and amino- acids, esters and amides and pharmaceutical compositions thereof |
| US4816473A (en) * | 1983-07-14 | 1989-03-28 | Syntex (U.S.A.) Inc. | Aroyl benzofuran and benzothiophene acetic and propionic acids |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1483061A (en) * | 1974-06-12 | 1977-08-17 | Schiapparelli Stabilment | Benzopyranyl-,naphtho-(2,1-6)furanyl-,and naphtho(2,1-6)pyranyl-substituted acetic and propionic acid derivatives |
-
1978
- 1978-09-05 IT IT03520/78A patent/IT1111639B/en active
-
1979
- 1979-08-24 AT AT79103127T patent/ATE148T1/en not_active IP Right Cessation
- 1979-08-24 EP EP79103127A patent/EP0008752B1/en not_active Expired
- 1979-08-24 DE DE7979103127T patent/DE2960637D1/en not_active Expired
- 1979-09-04 ES ES483856A patent/ES483856A1/en not_active Expired
- 1979-09-04 NO NO792850A patent/NO792850L/en unknown
- 1979-09-04 DK DK369479A patent/DK369479A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0008752A1 (en) | 1980-03-19 |
| NO792850L (en) | 1980-03-06 |
| EP0008752B1 (en) | 1981-08-12 |
| ES483856A1 (en) | 1980-04-16 |
| DK369479A (en) | 1980-03-06 |
| IT7803520A0 (en) | 1978-09-05 |
| IT1111639B (en) | 1986-01-13 |
| DE2960637D1 (en) | 1981-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| REN | Ceased due to non-payment of the annual fee |