CH507237A - Verfahren zur Herstellung von Indol-Derivaten - Google Patents
Verfahren zur Herstellung von Indol-DerivatenInfo
- Publication number
- CH507237A CH507237A CH278968A CH278968A CH507237A CH 507237 A CH507237 A CH 507237A CH 278968 A CH278968 A CH 278968A CH 278968 A CH278968 A CH 278968A CH 507237 A CH507237 A CH 507237A
- Authority
- CH
- Switzerland
- Prior art keywords
- indole
- alkyl
- hydrogen
- chlorobenzoyl
- methoxy
- Prior art date
Links
- 150000002475 indoles Chemical class 0.000 title claims description 4
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 3
- -1 hydroxy, amino Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical class C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 abstract description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- IURNVVIQOMTXSM-UHFFFAOYSA-N 4-chloro-n-(4-methoxyphenyl)benzohydrazide Chemical compound C1=CC(OC)=CC=C1N(N)C(=O)C1=CC=C(Cl)C=C1 IURNVVIQOMTXSM-UHFFFAOYSA-N 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HHVVFSZNIUHMEJ-UHFFFAOYSA-N 2-(1-benzoyl-5-methoxy-2-methylindol-3-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=CC=C1 HHVVFSZNIUHMEJ-UHFFFAOYSA-N 0.000 description 1
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical class C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
- ANYDSWOBDUWVHE-UHFFFAOYSA-N 4-chloro-n-(4-methoxyphenyl)benzohydrazide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1N(N)C(=O)C1=CC=C(Cl)C=C1 ANYDSWOBDUWVHE-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939467A GB1200483A (en) | 1967-02-28 | 1967-02-28 | Method and intermediates for producing indole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH507237A true CH507237A (de) | 1971-05-15 |
Family
ID=9871139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH278968A CH507237A (de) | 1967-02-28 | 1968-02-27 | Verfahren zur Herstellung von Indol-Derivaten |
Country Status (11)
| Country | Link |
|---|---|
| AT (2) | AT285597B (en。) |
| BE (1) | BE711306A (en。) |
| CH (1) | CH507237A (en。) |
| DE (1) | DE1670031A1 (en。) |
| ES (1) | ES351012A1 (en。) |
| FR (2) | FR1555227A (en。) |
| GB (1) | GB1200483A (en。) |
| IL (1) | IL29502A (en。) |
| NL (1) | NL6802698A (en。) |
| NO (1) | NO123386B (en。) |
| SE (1) | SE333732B (en。) |
-
1967
- 1967-02-28 GB GB939467A patent/GB1200483A/en not_active Expired
-
1968
- 1968-02-20 IL IL2950268A patent/IL29502A/xx unknown
- 1968-02-26 SE SE244668A patent/SE333732B/xx unknown
- 1968-02-26 DE DE19681670031 patent/DE1670031A1/de active Pending
- 1968-02-26 BE BE711306D patent/BE711306A/xx unknown
- 1968-02-26 NL NL6802698A patent/NL6802698A/xx unknown
- 1968-02-27 CH CH278968A patent/CH507237A/de not_active IP Right Cessation
- 1968-02-27 NO NO70868A patent/NO123386B/no unknown
- 1968-02-27 ES ES351012A patent/ES351012A1/es not_active Expired
- 1968-02-27 AT AT188568A patent/AT285597B/de not_active IP Right Cessation
- 1968-02-27 AT AT01410/69A patent/AT287689B/de not_active IP Right Cessation
- 1968-02-28 FR FR141585A patent/FR1555227A/fr not_active Expired
- 1968-05-28 FR FR153144A patent/FR7620M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT287689B (de) | 1971-02-10 |
| SE333732B (en。) | 1971-03-29 |
| FR7620M (en。) | 1970-01-26 |
| NL6802698A (en。) | 1968-08-29 |
| ES351012A1 (es) | 1969-05-16 |
| GB1200483A (en) | 1970-07-29 |
| NO123386B (en。) | 1971-11-08 |
| DE1670031A1 (de) | 1971-02-25 |
| AT285597B (de) | 1970-11-10 |
| BE711306A (en。) | 1968-07-01 |
| IL29502A (en) | 1971-10-20 |
| FR1555227A (en。) | 1969-01-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |