SU543344A3 - Способ получени 1-(п-хлорбензоил)-2метил-5-метоксииндолил-3-уксусной кислоты - Google Patents
Способ получени 1-(п-хлорбензоил)-2метил-5-метоксииндолил-3-уксусной кислотыInfo
- Publication number
- SU543344A3 SU543344A3 SU1419621A SU1419621A SU543344A3 SU 543344 A3 SU543344 A3 SU 543344A3 SU 1419621 A SU1419621 A SU 1419621A SU 1419621 A SU1419621 A SU 1419621A SU 543344 A3 SU543344 A3 SU 543344A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chlorobenzoyl
- acetic acid
- reaction mixture
- methoxyindolyl
- 2methyl
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 5
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 title description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 18
- 229940040102 levulinic acid Drugs 0.000 claims description 9
- -1 p-acetyl-p-methoxyphenylhydrazine Chemical compound 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 3
- 229940067157 phenylhydrazine Drugs 0.000 claims 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cookers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI000877 HU162374B (enrdf_load_stackoverflow) | 1969-04-03 | 1969-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU543344A3 true SU543344A3 (ru) | 1977-01-15 |
Family
ID=10994360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1419621A SU543344A3 (ru) | 1969-04-03 | 1970-04-02 | Способ получени 1-(п-хлорбензоил)-2метил-5-метоксииндолил-3-уксусной кислоты |
Country Status (11)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1338289C (en) * | 1986-01-22 | 1996-04-30 | Raymond August Murphy | Insecticidal n'-substituted-n-alkylcarbonyl- n'-acylhydrazines |
| TR23119A (tr) * | 1986-01-22 | 1989-04-03 | Rohm & Haas | Ensektisid n-suelostituee n-alkilharbonil-n 1-asil hidrazinler |
| CA1295618C (en) * | 1986-02-28 | 1992-02-11 | Adam Chi-Tung Hsu | Insecticidal n'-substituted-n-acyl -n'-alkylcarbonylhydrazines |
| US5106697A (en) * | 1989-04-17 | 1992-04-21 | Georgia-Pacific Resins, Inc. | Fast curing phenolic resin for making plywood |
| US5079332A (en) * | 1989-04-17 | 1992-01-07 | Georgia-Pacific Resins, Inc. | Fast curing phenolic resin for making plywood |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT290523B (de) * | 1962-01-05 | 1971-06-11 | Merck & Co Inc | Verfahren zur Herstellung neuer α-(3-Indolyl)-carbonsäuren |
| GB1148909A (en) * | 1965-04-19 | 1969-04-16 | Sumitomo Chemical Co | Process for production of novel phenylhydrazone and phenylhydrazine derivatives |
| AT262993B (de) * | 1965-04-19 | 1968-07-10 | Sumitomo Chemical Co | Verfahren zur Herstellung von zum Teil neuen aliphatischen (3-Indolyl)-carbonsäuren bzw. von funktionellen Derivaten derselben |
| IL27173A (en) * | 1966-01-12 | 1972-08-30 | Sumitomo Chemical Co | 1-carboxylic acyl-3-indolyl alkanoic acid derivatives and method for their preparation |
| FR1540725A (fr) * | 1966-10-13 | 1968-09-27 | Merck & Co Inc | Procédé pour la préparation d'acides indolyl-3-acétiques |
| NL6804994A (enrdf_load_stackoverflow) * | 1967-04-11 | 1968-10-14 |
-
1969
- 1969-04-03 HU HUCI000877 patent/HU162374B/hu unknown
- 1969-10-30 SE SE1486769A patent/SE380261B/xx unknown
-
1970
- 1970-02-28 DE DE19702009474 patent/DE2009474C2/de not_active Expired
- 1970-03-04 AT AT200170A patent/AT293377B/de active
- 1970-03-12 ES ES377421A patent/ES377421A1/es not_active Expired
- 1970-04-02 PL PL13976670A patent/PL97543B1/pl unknown
- 1970-04-02 NO NO122670A patent/NO136538C/no unknown
- 1970-04-02 SU SU1419621A patent/SU543344A3/ru active
- 1970-04-03 JP JP2854270A patent/JPS517666B1/ja active Pending
- 1970-04-03 CH CH499070A patent/CH555826A/xx not_active IP Right Cessation
- 1970-04-03 FR FR7012110A patent/FR2042302A1/fr active Granted
-
1972
- 1972-01-10 FR FR7200673A patent/FR2120185B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2120185A1 (enrdf_load_stackoverflow) | 1972-08-11 |
| FR2042302B1 (enrdf_load_stackoverflow) | 1975-10-31 |
| HU162374B (enrdf_load_stackoverflow) | 1973-02-28 |
| AT293377B (de) | 1971-10-11 |
| PL97543B1 (pl) | 1978-03-30 |
| FR2120185B1 (enrdf_load_stackoverflow) | 1975-10-10 |
| JPS517666B1 (enrdf_load_stackoverflow) | 1976-03-10 |
| DE2009474C2 (de) | 1984-05-10 |
| CH555826A (de) | 1974-11-15 |
| NO136538B (enrdf_load_stackoverflow) | 1977-06-13 |
| FR2042302A1 (en) | 1971-02-12 |
| ES377421A1 (es) | 1974-08-01 |
| SE380261B (sv) | 1975-11-03 |
| NO136538C (no) | 1977-09-21 |
| DE2009474A1 (de) | 1970-11-05 |
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