CH286498A - Verfahren zur Herstellung von 5-Keto-1,3,4,5-tetrahydro-benz(cd)indol. - Google Patents
Verfahren zur Herstellung von 5-Keto-1,3,4,5-tetrahydro-benz(cd)indol.Info
- Publication number
- CH286498A CH286498A CH286498DA CH286498A CH 286498 A CH286498 A CH 286498A CH 286498D A CH286498D A CH 286498DA CH 286498 A CH286498 A CH 286498A
- Authority
- CH
- Switzerland
- Prior art keywords
- benz
- keto
- indole
- tetrahydro
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- CAXVDGQDGNZJKF-UHFFFAOYSA-N 3,4-dihydro-1h-benzo[cd]indol-5-one Chemical compound C1=CC(C(=O)CC2)=C3C2=CNC3=C1 CAXVDGQDGNZJKF-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000008707 rearrangement Effects 0.000 claims description 4
- CAWUZNPMHOPWST-UHFFFAOYSA-N O=C1C2CC(C=3CCNC1=3)=CC=C2 Chemical compound O=C1C2CC(C=3CCNC1=3)=CC=C2 CAWUZNPMHOPWST-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PCWSNKLABDQTKE-UHFFFAOYSA-N [Ni+2].[O-][Cr]([O-])=O Chemical compound [Ni+2].[O-][Cr]([O-])=O PCWSNKLABDQTKE-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- -1 indoline 5-Keto-1,3,4,5-tetra-hydro-benz (cd) indole Chemical compound 0.000 description 1
- 150000002476 indolines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH286498T | 1950-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH286498A true CH286498A (de) | 1952-10-31 |
Family
ID=4530162
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH286498D CH286498A (de) | 1950-04-03 | 1950-04-03 | Verfahren zur Herstellung von 5-Keto-1,3,4,5-tetrahydro-benz(cd)indol. |
| CH291985D CH291985A (de) | 1950-04-03 | 1951-03-02 | Verfahren zur Herstellung von 5-Keto-1,3,4,5-tetrahydro-benz(cd)indol. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH291985D CH291985A (de) | 1950-04-03 | 1951-03-02 | Verfahren zur Herstellung von 5-Keto-1,3,4,5-tetrahydro-benz(cd)indol. |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH286498A (fr) |
| DE (1) | DE869342C (fr) |
| FR (1) | FR1045654A (fr) |
| GB (1) | GB702768A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE542760A (fr) * | 1954-11-12 |
-
1950
- 1950-04-03 CH CH286498D patent/CH286498A/de unknown
-
1951
- 1951-03-02 CH CH291985D patent/CH291985A/de unknown
- 1951-03-10 DE DE1951H0007996 patent/DE869342C/de not_active Expired
- 1951-04-02 GB GB7610/51A patent/GB702768A/en not_active Expired
- 1951-04-02 FR FR1045654D patent/FR1045654A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE869342C (de) | 1953-03-05 |
| FR1045654A (fr) | 1953-11-30 |
| CH291985A (de) | 1953-07-15 |
| GB702768A (en) | 1954-01-20 |
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