http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-629282-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_c7d5c623c321062f7907ef560288c36e http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_1a768094ac38271abd061207c1d4f27c |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D215-233 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D215-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D215-56 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D215-46 |
| classificationIPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D215-22 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D215-46 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D215-233 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D215-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D215-56 |
| filingDate | 1946-10-18-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1949-09-15-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-629282-A |
| titleOfInvention | Method of manufacturing substituted quinolines |
| abstract | A 4-amino substituted quinoline is prepared by heating, e.g. at about 100 to 125 DEG C. for about 2 to 6 hours, approximately equimolar proportions of a dialkyl malonate and a diphenyl formamidine of the general formula ArNH-CH=NAr, wherein each Ar is a substituted or unsubstituted phenyl group, to produce a phenylamino methylene malonic ester of the general formula ArNH-CH= C(COOR)2 or its isomeric anil ArN=CH-CH(COOR)2, wherein R is an alkyl group, but insufficient to produce a substantial proportion of the amide-ester derivative of said malonic ester of the formula ArNH-CH=C(COOR)-CONHAr, heating the phenylamino methylene malonic ester or its isomeric anil to form a 3-carbalkoxy-4-hydroxy quinoline, hydrolysing the ester to the free carboxylic acid, decarboxylating the acid to produce a 7-hydroxyquinaline, treating the 4-hydroxyquinoline with a chlorinating or brominating agent to produce a 4-haloquinoline which is reacted with a compound containing a primary or secondary amino group to yield a 4-amino substituted quinoline. The phenylamino methylene malonic ester containing product obtained as above may be mixed with aqueous hydrochloric acid and a water immiscible, preferably volatile solvent, e.g. benzene, for the ester to precipitate the hydrochloride of unreacted formamidine. The resulting solution in the solvent is separated from the water and undissolved matter, and the volatile components including the solvent if volatile are removed from the solute. The phenylamino methylene malonic ester or its isomeric anil may be cyclised by heating in a high boiling solvent, e.g. diphenyl ether, at about 250 DEG C., the said high boiling solvent may be the same as the water immiscible solvent in which the phenylamino methylene malonic ester product is formed. The 3-carbalkoxy-4-hydroxy quinoline containing product of the above process may be saponified with aqueous alkali and unchanged anilide separated therefrom may then be hydrolysed with aqueous sulphuric acid containing approximately 75 per cent sulphuric acid. In examples, 4 : 7-dichloroquinaline is prepared by the above procedure and is condensed with 1-diethylamino - 4 - aminopentane, or 1 - di-ethylamino-2-aminoethane. 4-Diethylaminobutylamine is given as an additional example of an amine containing a primary or secondary amino group. Other substituents which may be present in the phenyl ring are alkyl, e.g. methyl, alkoxy, e.g. methoxy or ethoxy, aryloxy, e.g. phenoxy, benzo, carbalkoxy, e.g. carbethoxy, cyano or nitro groups. The Specification as open to inspection under Sect. 91 refers to the above process wherein the group Ar may represent any aryl group. Other amines containing a primary or secondary amino group mentioned are 3-diethylamino-propyl-amine and 3-diethylamino-2-hydroxy-propylamine. This subject-matter does not appear in the Specification as accepted. |
| priorityDate | 1946-03-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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Total number of triples: 58.