http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-633266-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_fd9f36df06271a59df790e5021907cdc |
| filingDate | 1948-02-11-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1949-12-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-633266-A |
| titleOfInvention | Process for the manufacture of 5,6,7,8-tetrahydroisoquinoline |
| abstract | 5,6,7,8-Tetrahydroisoquinoline is obtained by condensing, preferably in the presence of sodium ethylate, aminomethylene-cyclohexanone with a malonic alkyl, preferably ethyl, ester, saponifying and decarboxylating the resulting 3 - hydroxy - 5,6,7,8 - tetrahydroisoquinoline - 4 - carboxylic-acid-ester with dilute hydrochloric acid and converting the 3-hydroxy-5,6,7,8-tetrahydroisoquinoline so formed into the corresponding 3-chloro-compound by treatment with a chlorinating agent and dechlorinating the said 3-chloro-compound by hydrogenation. In an example, 2-aminomethylenecyclohexanone is added to an alcoholic solution of ethyl malonate and sodium ethylate at 50 DEG C., the sodium salt of p 3-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carboxylic-acid-ethyl ester obtained is converted by acidification with acetic acid to the free acid, which is collected and after recrystallization is saponified and decarboxylated by boiling with dilute hydrochloric acid when excess acid is removed and the 3 - hydroxy - 5,6,7,8 - tetrahydroisoquinoline-hydrochloride obtained is converted to the free base by treatment with dilute ammonium hydroxide, after recrystallization the free base is treated with phosphorus oxychloride in an autocalve for 3 hours at 170-180 DEG C., and after isolation and purification the 3-chloro-compound so formed is hydrogenated in methanol solution with a palladium charcoal catalyst under slightly elevated pressure to give 5,6,7,8 - tetrahydroisoquinoline - hydrochloride, which is converted to the free base with sodium hydroxide solution. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4332940-A |
| priorityDate | 1947-02-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 38.