JPH0212220B2 - - Google Patents

Info

Publication number

JPH0212220B2

JPH0212220B2 JP56204099A JP20409981A JPH0212220B2 JP H0212220 B2 JPH0212220 B2 JP H0212220B2 JP 56204099 A JP56204099 A JP 56204099A JP 20409981 A JP20409981 A JP 20409981A JP H0212220 B2 JPH0212220 B2 JP H0212220B2

Authority

JP

Japan

Prior art keywords

indole

cyclodextrin

aldehyde

reaction

selectivity

Prior art date

1981-12-17

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.)

Expired - Lifetime

Links

• Espacenet
• Global Dossier
• Discuss

• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
• 229920000858 Cyclodextrin Polymers 0.000 claims description 12
• OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 claims description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 9
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
• 238000000034 method Methods 0.000 claims description 5
• 239000003054 catalyst Substances 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 15
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 239000000243 solution Substances 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• FLORQCMDMHHIHN-UHFFFAOYSA-N 3-chloroquinoline Chemical compound C1=CC=CC2=CC(Cl)=CN=C21 FLORQCMDMHHIHN-UHFFFAOYSA-N 0.000 description 3
• 239000001116 FEMA 4028 Substances 0.000 description 3
• WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 3
• 235000011175 beta-cyclodextrine Nutrition 0.000 description 3
• 229960004853 betadex Drugs 0.000 description 3
• 239000007789 gas Substances 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 230000000052 comparative effect Effects 0.000 description 2
• 239000002994 raw material Substances 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
• 229920001353 Dextrin Polymers 0.000 description 1
• 239000004375 Dextrin Substances 0.000 description 1
• 239000003905 agrochemical Substances 0.000 description 1
• HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
• 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 239000012159 carrier gas Substances 0.000 description 1
• -1 cyclic oligosaccharide Chemical class 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 235000019425 dextrin Nutrition 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 239000001307 helium Substances 0.000 description 1
• 229910052734 helium Inorganic materials 0.000 description 1
• SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 229920001542 oligosaccharide Polymers 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000006049 ring expansion reaction Methods 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1