DE1950219B2 - Verfahren zur herstellung von reinem 4-amino- und 5-aminoindan - Google Patents
Verfahren zur herstellung von reinem 4-amino- und 5-aminoindanInfo
- Publication number
- DE1950219B2 DE1950219B2 DE19691950219 DE1950219A DE1950219B2 DE 1950219 B2 DE1950219 B2 DE 1950219B2 DE 19691950219 DE19691950219 DE 19691950219 DE 1950219 A DE1950219 A DE 1950219A DE 1950219 B2 DE1950219 B2 DE 1950219B2
- Authority
- DE
- Germany
- Prior art keywords
- aminoindane
- mixture
- pure
- nitroindane
- ligroin
- Prior art date
- 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.)
- Granted
Links
- RXTJLDXSGNEJIT-UHFFFAOYSA-N 2,3-dihydro-1h-inden-4-amine Chemical compound NC1=CC=CC2=C1CCC2 RXTJLDXSGNEJIT-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 12
- LEWZOBYWGWKNCK-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-amine Chemical compound NC1=CC=C2CCCC2=C1 LEWZOBYWGWKNCK-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 12
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 claims description 6
- ZQABKMBXKCJTPM-UHFFFAOYSA-N 4-nitro-2,3-dihydro-1h-indene Chemical compound [O-][N+](=O)C1=CC=CC2=C1CCC2 ZQABKMBXKCJTPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000001384 succinic acid Substances 0.000 claims description 6
- DUROKJUTAMUPAH-UHFFFAOYSA-N 1-nitro-2,3-dihydro-1h-indene Chemical compound C1=CC=C2C([N+](=O)[O-])CCC2=C1 DUROKJUTAMUPAH-UHFFFAOYSA-N 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 238000006396 nitration reaction Methods 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- DLURUQQMVLOLCP-UHFFFAOYSA-N 5-nitro-2,3-dihydro-1h-indene Chemical compound [O-][N+](=O)C1=CC=C2CCCC2=C1 DLURUQQMVLOLCP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012454 non-polar solvent Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- -1 succinic acid 5-Aminoindan Chemical compound 0.000 description 3
- HHGHVFAOCLPZQG-UHFFFAOYSA-N 2-(5-amino-2,3-dihydro-1H-inden-1-yl)butanedioic acid Chemical compound NC1=CC=C(C(CC2)C(CC(O)=O)C(O)=O)C2=C1 HHGHVFAOCLPZQG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LCDAXSHKIIADOP-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-5-yl)methanimine Chemical compound C=NC1=CC=C2CCCC2=C1 LCDAXSHKIIADOP-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691950219 DE1950219B2 (de) | 1969-10-04 | 1969-10-04 | Verfahren zur herstellung von reinem 4-amino- und 5-aminoindan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691950219 DE1950219B2 (de) | 1969-10-04 | 1969-10-04 | Verfahren zur herstellung von reinem 4-amino- und 5-aminoindan |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1950219A1 DE1950219A1 (de) | 1971-04-15 |
| DE1950219B2 true DE1950219B2 (de) | 1977-08-25 |
| DE1950219C3 DE1950219C3 (enrdf_load_stackoverflow) | 1978-04-27 |
Family
ID=5747386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691950219 Granted DE1950219B2 (de) | 1969-10-04 | 1969-10-04 | Verfahren zur herstellung von reinem 4-amino- und 5-aminoindan |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1950219B2 (enrdf_load_stackoverflow) |
-
1969
- 1969-10-04 DE DE19691950219 patent/DE1950219B2/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE1950219C3 (enrdf_load_stackoverflow) | 1978-04-27 |
| DE1950219A1 (de) | 1971-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1804691C3 (de) | Taurocholensäurederivate | |
| EP0001274B1 (de) | Verfahren zur Herstellung von Serinol | |
| DE2903891A1 (de) | Optisch aktive benzamide, verfahren zu deren herstellung und deren anwendung | |
| DE1950219C3 (enrdf_load_stackoverflow) | ||
| DE1957259C3 (de) | Verfahren zur Herstellung von reinem 4-Amino- und 5-Aminoindan | |
| DE3729471A1 (de) | Verfahren zur herstellung von guanin | |
| DE865739C (de) | Verfahren zur Herstellung von Monochloressigsaeure | |
| DE348484C (de) | Verfahren zur Darstellung des wahren Camphenchlorhydrats | |
| DE2654851C2 (de) | Verfahren zur Herstellung von α, β-ungesättigten cycloaliphatischen Ketoximen mit 6 Kohlenstoffatomen im Ring | |
| DE753213C (de) | Verfahren zur synthetischen Gewinnung des Corpusluteum-Hormons | |
| DE857501C (de) | Verfahren zur Herstellung von Disulfiden | |
| DE913779C (de) | Verfahren zur Herstellung eines Oxyphenyl-aethanolamins | |
| DE708114C (de) | Verfahren zur Herstellung eines Oxotetrahydronaphthalins | |
| DE301870C (enrdf_load_stackoverflow) | ||
| AT275735B (de) | Verfahren zur Reinigung von a-6-Deoxy-5-oxy-tetracyclin | |
| AT244324B (de) | Verfahren zur Herstellung von Cycloalkanonoximen | |
| DE695317C (de) | Verfahren zur Gewinnung des Adenosins aus dem entsprechenden Pikrat | |
| AT142359B (de) | Verfahren zur Herstellung von Hydrierungsprodukten der aus tierischem oder pflanzlichem Material oder auf synthetischem Wege erhaltenen Follikelhormone. | |
| DE606615C (de) | Verfahren zur Herstellung von Tetrazolabkoemmlingen der Terpenreihe | |
| DE734621C (de) | Verfahren zur Darstellung von Hydrierungsprodukten des Follikelhormons | |
| AT160395B (de) | Verfahren zur Darstellung von Monohalogenverbindungen gesättigter Ketone bzw. von ungesättigten Ketonen der Pregnanreihe. | |
| DE932796C (de) | Verfahren zur Herstellung von gesaettigten und ungesaettigten 17-Oxy-20-ketonen der Pregnanreihe | |
| DE698910C (de) | gmasterin | |
| DE951628C (de) | Verfahren zur Herstellung von 3-Aminoindanen | |
| AT258480B (de) | Verfahren zur Herstellung von racemischen und optisch aktiven 2-Dehydro-emetinverbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |