Reduction of Ethyl Indoxylate. I. Catalytic Reduction of Acetyl Derivatives of Ethyl Indoxylate
The high-pressure catalytic hydrogenation of the acetyl derivatives of ethyl indoxylate was investigated. Under 85 atms. of hydrogen atmosphere at 100∼110°, nickel catalyst converted ethyl 3-acetoxyindole-2-carboxylate (V) into ethyl 3-acetoxy-4, 5, 6, 7-tetrahydroindole-2 -carboxylate (IX), and eth...
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| Veröffentlicht in: | Pharmaceutical Bulletin 1956/08/25, Vol.4(4), pp.261-266 |
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| container_title | Pharmaceutical Bulletin |
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| creator | KOMAI, Tomoyoshi |
| description | The high-pressure catalytic hydrogenation of the acetyl derivatives of ethyl indoxylate was investigated. Under 85 atms. of hydrogen atmosphere at 100∼110°, nickel catalyst converted ethyl 3-acetoxyindole-2-carboxylate (V) into ethyl 3-acetoxy-4, 5, 6, 7-tetrahydroindole-2 -carboxylate (IX), and ethyl 1-acetyl-3-acetoxyindole-2-carboxylate (VI) into ethyl 1-acetylindoline-2-carboxylate (XI), but ethyl 1 -acetylindoxylate (VIII) was hydrogenated to ethyl 1-acetyl-3-hydroxyindoline-2-carboxylate (XIII) at 60 atms. and 60°, and to ethyl 1-acetyl-3-hydroxyoctahydroindole-2-carboxylate (XIX) at 150 atms. and 110∼120°. |
| doi_str_mv | 10.1248/cpb1953.4.261 |
| format | Article |
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I. Catalytic Reduction of Acetyl Derivatives of Ethyl Indoxylate</title><title>Pharmaceutical Bulletin</title><addtitle>Pharmaceutical Bulletin</addtitle><description>The high-pressure catalytic hydrogenation of the acetyl derivatives of ethyl indoxylate was investigated. Under 85 atms. of hydrogen atmosphere at 100∼110°, nickel catalyst converted ethyl 3-acetoxyindole-2-carboxylate (V) into ethyl 3-acetoxy-4, 5, 6, 7-tetrahydroindole-2 -carboxylate (IX), and ethyl 1-acetyl-3-acetoxyindole-2-carboxylate (VI) into ethyl 1-acetylindoline-2-carboxylate (XI), but ethyl 1 -acetylindoxylate (VIII) was hydrogenated to ethyl 1-acetyl-3-hydroxyindoline-2-carboxylate (XIII) at 60 atms. and 60°, and to ethyl 1-acetyl-3-hydroxyoctahydroindole-2-carboxylate (XIX) at 150 atms. and 110∼120°.</description><subject>Catalysis</subject><subject>Indoles - analogs & derivatives</subject><subject>Old Medline</subject><issn>0369-9471</issn><issn>1881-1345</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1956</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM9LwzAUgIMobswdvUpP3lqbH23T45hTBwNB9BzS5NV1dO1M0mH_eyMtTsGXw3uQj-_wIXSN4wgTxu_UocB5QiMWkRSfoSnmHIeYsuQcTWOa5mHOMjxBc2t3sZ-EZTmJL9EEU5rxnPEpEi-gO-WqtgnaMli5bV8H60a3n30tHUTBOgqW0sm6d5UK_rALBc7D92Cqo3TVEex_hit0UcrawnzcM_T2sHpdPoWb58f1crEJFaEUh5RqWRKeMpKplBcc66TwN6GEK16yUmUsUUlJSq1lwYDGRDMmcaY451ISoDN0O3gPpv3owDqxr6yCupYNtJ0VHGeM53HiwXAAlWmtNVCKg6n20vQCx-I7qhijCiZ8VM_fjOKu2IM-0WNCDywGYGedfIcfQBqfrIZfuuF56elvK42Ahn4BXXWJsg</recordid><startdate>195608</startdate><enddate>195608</enddate><creator>KOMAI, Tomoyoshi</creator><general>The Pharmaceutical Society of Japan</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>195608</creationdate><title>Reduction of Ethyl Indoxylate. 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Catalytic Reduction of Acetyl Derivatives of Ethyl Indoxylate</title><author>KOMAI, Tomoyoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2331-33daf286427c68b81d5b4272328c8f4fc745c5f2fddab4e302d44a17c888aa2e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1956</creationdate><topic>Catalysis</topic><topic>Indoles - analogs & derivatives</topic><topic>Old Medline</topic><toplevel>online_resources</toplevel><creatorcontrib>KOMAI, Tomoyoshi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KOMAI, Tomoyoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reduction of Ethyl Indoxylate. 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| fulltext | fulltext |
| identifier | ISSN: 0369-9471 |
| ispartof | Pharmaceutical Bulletin, 1956/08/25, Vol.4(4), pp.261-266 |
| issn | 0369-9471 1881-1345 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_81748905 |
| source | MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Catalysis Indoles - analogs & derivatives Old Medline |
| title | Reduction of Ethyl Indoxylate. I. Catalytic Reduction of Acetyl Derivatives of Ethyl Indoxylate |
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