SU620208A3 - Способ получени производных индола - Google Patents
Способ получени производных индолаInfo
- Publication number
- SU620208A3 SU620208A3 SU762364003A SU2364003A SU620208A3 SU 620208 A3 SU620208 A3 SU 620208A3 SU 762364003 A SU762364003 A SU 762364003A SU 2364003 A SU2364003 A SU 2364003A SU 620208 A3 SU620208 A3 SU 620208A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydrogen
- halogen
- carbonitrile
- phenyl
- alkoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 229940054051 antipsychotic indole derivative Drugs 0.000 title claims description 4
- 150000002475 indoles Chemical class 0.000 title claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- -1 methylenedioxy group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 2
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- CKJUHALNJRNCLY-UHFFFAOYSA-N 3-(2-fluorophenyl)-5-methoxy-1h-indole-2-carbonitrile Chemical compound C12=CC(OC)=CC=C2NC(C#N)=C1C1=CC=CC=C1F CKJUHALNJRNCLY-UHFFFAOYSA-N 0.000 description 1
- MXHLTBZQERCPAP-UHFFFAOYSA-N 3-nitro-1H-indole-2-carbonitrile Chemical compound C1=CC=C2C([N+](=O)[O-])=C(C#N)NC2=C1 MXHLTBZQERCPAP-UHFFFAOYSA-N 0.000 description 1
- QNPFATMHMDYSKJ-UHFFFAOYSA-N 3-phenyl-6-(trifluoromethyl)-1h-indole-2-carbonitrile Chemical compound N#CC=1NC2=CC(C(F)(F)F)=CC=C2C=1C1=CC=CC=C1 QNPFATMHMDYSKJ-UHFFFAOYSA-N 0.000 description 1
- WPITURUTRWMEEC-UHFFFAOYSA-N 5,7-dichloro-3-phenyl-1h-indole-2-carbonitrile Chemical compound C12=CC(Cl)=CC(Cl)=C2NC(C#N)=C1C1=CC=CC=C1 WPITURUTRWMEEC-UHFFFAOYSA-N 0.000 description 1
- XGOWHPSXPPZWAH-UHFFFAOYSA-N 5-bromo-2-phenyl-1h-indole Chemical compound C=1C2=CC(Br)=CC=C2NC=1C1=CC=CC=C1 XGOWHPSXPPZWAH-UHFFFAOYSA-N 0.000 description 1
- JCWKJDGGBPKHPS-UHFFFAOYSA-N 5-bromo-3-phenyl-1h-indole-2-carbonitrile Chemical compound C12=CC(Br)=CC=C2NC(C#N)=C1C1=CC=CC=C1 JCWKJDGGBPKHPS-UHFFFAOYSA-N 0.000 description 1
- LWFZLPUSRONGSO-UHFFFAOYSA-N 5-chloro-3-(2-fluorophenyl)-1h-indole-2-carbonitrile Chemical compound FC1=CC=CC=C1C1=C(C#N)NC2=CC=C(Cl)C=C12 LWFZLPUSRONGSO-UHFFFAOYSA-N 0.000 description 1
- QWCNAXBXVVZXGZ-UHFFFAOYSA-N 5-chloro-3-phenyl-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1C1=CC=CC=C1 QWCNAXBXVVZXGZ-UHFFFAOYSA-N 0.000 description 1
- SUKNESIOLWWYKH-UHFFFAOYSA-N 5-methoxy-3-phenyl-1h-indole-2-carbonitrile Chemical compound C12=CC(OC)=CC=C2NC(C#N)=C1C1=CC=CC=C1 SUKNESIOLWWYKH-UHFFFAOYSA-N 0.000 description 1
- GKVAJGVNECYSGK-UHFFFAOYSA-N 5-methyl-3-phenyl-1h-indole-2-carbonitrile Chemical compound C12=CC(C)=CC=C2NC(C#N)=C1C1=CC=CC=C1 GKVAJGVNECYSGK-UHFFFAOYSA-N 0.000 description 1
- LOKVESWSNJFXJO-UHFFFAOYSA-N 5-nitro-1H-indole-2-carbonitrile Chemical compound [N+](=O)([O-])C=1C=C2C=C(NC2=CC=1)C#N LOKVESWSNJFXJO-UHFFFAOYSA-N 0.000 description 1
- PHEBSBWKWVRKMJ-UHFFFAOYSA-N 6-chloro-3-phenyl-1h-indole-2-carbonitrile Chemical compound N#CC=1NC2=CC(Cl)=CC=C2C=1C1=CC=CC=C1 PHEBSBWKWVRKMJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-N PYRUVIC-ACID Natural products CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940088623 biologically active substance Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical group COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6776575A JPS51143665A (en) | 1975-06-04 | 1975-06-04 | A novel process for preparing 2- cyanoindole derivatives |
| JP7005675A JPS51146460A (en) | 1975-06-09 | 1975-06-09 | A novel process for preparing 2-cyano-5- nitroindole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU620208A3 true SU620208A3 (ru) | 1978-08-15 |
Family
ID=26408979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762364003A SU620208A3 (ru) | 1975-06-04 | 1976-06-03 | Способ получени производных индола |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4069230A (OSRAM) |
| AT (1) | AT352110B (OSRAM) |
| CA (1) | CA1071637A (OSRAM) |
| CH (1) | CH602639A5 (OSRAM) |
| DD (1) | DD126311A5 (OSRAM) |
| DE (1) | DE2625029A1 (OSRAM) |
| FR (1) | FR2313365A1 (OSRAM) |
| GB (1) | GB1494888A (OSRAM) |
| HU (1) | HU173660B (OSRAM) |
| MX (1) | MX3179E (OSRAM) |
| NL (1) | NL7605382A (OSRAM) |
| SE (1) | SE406586B (OSRAM) |
| SU (1) | SU620208A3 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2745977C2 (ru) * | 2010-04-22 | 2021-04-05 | Вертекс Фармасьютикалз Инкорпорейтед | Способ получения циклоалкилкарбоксамидо-индольных соединений |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL97873A0 (en) * | 1990-04-16 | 1992-06-21 | Yissum Res Dev Co | Heterocyclicethenediyl compounds which inhibit egf receptor tyrosine kinase |
| US5118695A (en) * | 1990-08-06 | 1992-06-02 | Eastman Kodak Company | 1-hydroxyindole fungicides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3632573A (en) * | 1967-10-09 | 1972-01-04 | Sumitomo Chemical Co | Method for producing benzodiazepine derivatives |
| US3790596A (en) * | 1971-05-14 | 1974-02-05 | V Shkilkova | Method of producing indole and substitution products of the same |
-
1976
- 1976-05-20 NL NL7605382A patent/NL7605382A/xx not_active Application Discontinuation
- 1976-05-31 AT AT398076A patent/AT352110B/de not_active IP Right Cessation
- 1976-06-01 US US05/691,777 patent/US4069230A/en not_active Expired - Lifetime
- 1976-06-01 FR FR7616480A patent/FR2313365A1/fr active Granted
- 1976-06-01 GB GB22667/76A patent/GB1494888A/en not_active Expired
- 1976-06-02 MX MX000258U patent/MX3179E/es unknown
- 1976-06-02 CH CH696676A patent/CH602639A5/xx not_active IP Right Cessation
- 1976-06-03 HU HU76SU915A patent/HU173660B/hu unknown
- 1976-06-03 SE SE7606271A patent/SE406586B/xx unknown
- 1976-06-03 SU SU762364003A patent/SU620208A3/ru active
- 1976-06-03 DD DD193159A patent/DD126311A5/xx unknown
- 1976-06-03 DE DE19762625029 patent/DE2625029A1/de not_active Withdrawn
- 1976-06-03 CA CA253,965A patent/CA1071637A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2745977C2 (ru) * | 2010-04-22 | 2021-04-05 | Вертекс Фармасьютикалз Инкорпорейтед | Способ получения циклоалкилкарбоксамидо-индольных соединений |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7605382A (nl) | 1976-12-07 |
| SE7606271L (sv) | 1976-12-05 |
| MX3179E (es) | 1980-06-11 |
| FR2313365B1 (OSRAM) | 1978-06-30 |
| US4069230A (en) | 1978-01-17 |
| HU173660B (hu) | 1979-07-28 |
| GB1494888A (en) | 1977-12-14 |
| AT352110B (de) | 1979-09-10 |
| DD126311A5 (OSRAM) | 1977-07-06 |
| CA1071637A (en) | 1980-02-12 |
| SE406586B (sv) | 1979-02-19 |
| FR2313365A1 (fr) | 1976-12-31 |
| ATA398076A (de) | 1979-02-15 |
| DE2625029A1 (de) | 1976-12-30 |
| CH602639A5 (OSRAM) | 1978-07-31 |
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