JPS5576859A - Novel preparation of 4-hydroxyindole - Google Patents
Novel preparation of 4-hydroxyindoleInfo
- Publication number
- JPS5576859A JPS5576859A JP14941478A JP14941478A JPS5576859A JP S5576859 A JPS5576859 A JP S5576859A JP 14941478 A JP14941478 A JP 14941478A JP 14941478 A JP14941478 A JP 14941478A JP S5576859 A JPS5576859 A JP S5576859A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyindole
- cyanomethyl
- carboxylic acid
- nitrobenzene
- novel preparation
- 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.)
- Pending
Links
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 title abstract 2
- -1 2-cyanomethyl-3-substituted methoxy-nitrobenzene Chemical class 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 2
- SPCIYGNTAMCTRO-UHFFFAOYSA-N Psilocine Natural products C1=CC(O)=C2C(CCN(C)C)=CNC2=C1 SPCIYGNTAMCTRO-UHFFFAOYSA-N 0.000 abstract 1
- 238000005574 benzylation reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 abstract 1
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 abstract 1
- 229960002508 pindolol Drugs 0.000 abstract 1
- ZBWSBXGHYDWMAK-UHFFFAOYSA-N psilocin Chemical compound C1=CC=C(O)[C]2C(CCN(C)C)=CN=C21 ZBWSBXGHYDWMAK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Landscapes
- Indole Compounds (AREA)
Abstract
PURPOSE: To obtain the title compound useful as a raw material for drugs, Pindolol or Psilocin, in one step, by catalytic reduction of a 2-cyanomethyl-3-substituted methoxy-nitrobenzene in the presence of an aromatic carboxylic acid.
CONSTITUTION: A 2-cyanomethyl-3-substituted methoxy nitrobenzene is subjected to catalytic reduction in the presence of an aromatic carboxylic acid and palladium carbon in a solvent in an autoclave through ring closure and benzylation to give 4-hydroxyindole in one step.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14941478A JPS5576859A (en) | 1978-12-01 | 1978-12-01 | Novel preparation of 4-hydroxyindole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14941478A JPS5576859A (en) | 1978-12-01 | 1978-12-01 | Novel preparation of 4-hydroxyindole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5576859A true JPS5576859A (en) | 1980-06-10 |
Family
ID=15474589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14941478A Pending JPS5576859A (en) | 1978-12-01 | 1978-12-01 | Novel preparation of 4-hydroxyindole |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5576859A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1000762A5 (en) * | 1986-11-07 | 1989-03-28 | Oreal | PROCESS FOR THE PREPARATION OF 5,6-DIHYDROXYINDOLE AND ITS 3-ALKYL DERIVATIVE AND INTERMEDIATE COMPOUNDS. |
| US10519175B2 (en) | 2017-10-09 | 2019-12-31 | Compass Pathways Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11564935B2 (en) | 2019-04-17 | 2023-01-31 | Compass Pathfinder Limited | Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
| US12459965B2 (en) | 2017-10-09 | 2025-11-04 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5289668A (en) * | 1975-12-09 | 1977-07-27 | Dumex Ltd As | Production of heterocyclic compound |
-
1978
- 1978-12-01 JP JP14941478A patent/JPS5576859A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5289668A (en) * | 1975-12-09 | 1977-07-27 | Dumex Ltd As | Production of heterocyclic compound |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1000762A5 (en) * | 1986-11-07 | 1989-03-28 | Oreal | PROCESS FOR THE PREPARATION OF 5,6-DIHYDROXYINDOLE AND ITS 3-ALKYL DERIVATIVE AND INTERMEDIATE COMPOUNDS. |
| US12312375B2 (en) | 2017-10-09 | 2025-05-27 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11851451B2 (en) | 2017-10-09 | 2023-12-26 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US10954259B1 (en) | 2017-10-09 | 2021-03-23 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11149044B2 (en) | 2017-10-09 | 2021-10-19 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11180517B2 (en) | 2017-10-09 | 2021-11-23 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11447510B2 (en) | 2017-10-09 | 2022-09-20 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11505564B2 (en) | 2017-10-09 | 2022-11-22 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US12459965B2 (en) | 2017-10-09 | 2025-11-04 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US10947257B2 (en) | 2017-10-09 | 2021-03-16 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11939346B2 (en) | 2017-10-09 | 2024-03-26 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11629159B2 (en) | 2017-10-09 | 2023-04-18 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US10519175B2 (en) | 2017-10-09 | 2019-12-31 | Compass Pathways Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US12377112B2 (en) | 2019-04-17 | 2025-08-05 | Compass Pathfinder Limited | Methods of treating neurocognitive disorders, chronic pain and reducing inflammation |
| US12433904B2 (en) | 2019-04-17 | 2025-10-07 | Compass Pathfinder Limited | Methods for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
| US12447164B2 (en) | 2019-04-17 | 2025-10-21 | Compass Pathfinder Limited | Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
| US11564935B2 (en) | 2019-04-17 | 2023-01-31 | Compass Pathfinder Limited | Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
| US12611418B2 (en) | 2019-04-17 | 2026-04-28 | Compass Pathfinder Limited | Methods for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
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