http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1187817-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_d202e9e866984fe229f6facc38f1d740 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D209-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D209-26 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D209-28 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D209-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D209-28 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D209-26 |
| filingDate | 1967-11-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_64057abbe333082e8e1d423d9d6d272e http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_74cd37b660740f760e791d8b679f1616 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_7ce1ae47a9b2c6669b714b82cef89644 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_c033041fbdd635d86e3ab9ecc426e76b |
| publicationDate | 1970-04-15-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1187817-A |
| titleOfInvention | Production of Indole Derivatives |
| abstract | 1,187,817. Indole derivatives. MERCK & CO. Inc. 6 Nov., 1967 [14 Nov., 1966], No. 50360/67. Heading C2C. The compounds are made by reacting (1) a p-nitro-R 2 -substituted phenylhydrazine with an α-R 1 -substituted levulinic acid; or (2) a p-nitro-R 2 -substituted phenylhydrazone of an α-R 1 -substituted levulinic acid, in a reaction mixture containing 30% to 55% by weight hydrochloric acid at a temp. of from 50 to 80 C. for 8 to 120 hrs. in a sealed vessel. R 1 is a hydrogen atom or C 1-6 alkyl radical and R 2 is a hydrogen or halogen atom or C 1-6 alkyl radical. The preparation of a number of such compounds, including chloro and fluoro derivatives, is described. The products may be converted to the therapeutically useful N-acylated derivatives. α-[1-(p- Chlorobenzoyl) - 2 - methyl - 5 - amino - 3 - indolyl]-acetic acid is obtained by treating 2- methyl - 5 - nitro - 3 - indolyl acetic acid with N,N-dicyclohexylcarbodiimide to form 2-methyl- 5 - nitro - 3 - indolyl acetic anhydride which is reacted with t-butanol to obtain t-butyl (2- methyl - 5 - nitro - 3 - indolyl] acetate which is N-acylated with p-chlorobenzoyl chloride in the presence of sodium hydride to obtain t-butyl [1 - (p - chlorobenzoyl) - 2 - methyl - 5 - nitro - 3- indolyl] acetate which on reduction with hydrogen over Pd/charcoal yields t-butyl [1-(p-chlorobenzoyl) - 2 - methyl - 5 - amino - 3 - indolyl] acetate which on heating yields the above acid with evolution of isobutylene-α-[1-(p-thiomethylbenzoyl) - 2 - methyl - 5 - dimethylamino - 3- indolyl] acetic acid is obtained by a similar process starting from t-butyl (2-methyl-6-dimethylamino - 3 - indolyl) acetate, obtained by Raney nickel reduction of t-butyl (2-methyl- 5 - nitro - 3 - indolyl) acetate in the presence of formaldehyde. |
| priorityDate | 1966-11-14-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 50.