http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-672727-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_dc2f7134efa50484bb359fda73782848 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C57-40 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C57-40 |
| filingDate | 1949-08-02-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1952-05-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-672727-A |
| titleOfInvention | Manufacture of new naphthyl-propionic acids and functional derivatives thereof |
| abstract | b - (2 - Naphthyl) - a : a : b - trialkylpropionic acids unsubstituted in the 6-position of the naphthalene ring, and esters and nitriles thereof, are manufactured from 2-naphthyl alkyl ketones (unsubstituted in the 6-position) by reaction in the presence of a metal (and preferably also an inert solvent) with a halogen-acetic acid ester, of which the acetic acid residue is not further substituted or is mono- or di-alkylated, replacement of the hydroxy group in the resulting tertiary carbinol by hydrogen (directly, e.g. by heating with hydrogen iodide and red phosphorus, or indirectly, e.g. by dehydration followed by hydrogenation), or by replacement of the carbonyl group by a halogen-methylene group by reduction to the carbinol and replacement of the hydroxy group by halogen, reaction of the resulting 2-naphthylalkylmethyl halide in the presence of a metal with a halogen-acetic acid ester which may be mono- or di-alkylated in the acetic acid residue and, in either case, when necessary, introduction into the a -position of the propionic residue of any alkyl group which may be lacking (e.g. by the action of an alkyl halide, advantageously in the presence of sodium triphenylmethyl and an inert organic solvent); or from esters or nitriles of (2-naphthoyl)-dialkylacetic acids (unsubstituted in the 6-position) by reaction with a metal compound of an aliphatic hydrocarbon and replacement of the hydroxy group in the resulting carbinol by hydrogen (if desired after hydrogenating aliphatic carbon-to-carbon multiple bonds), or by reaction in the presence of a metal with an ester of a halogen-acetic or b -halogen-propionic acid, replacement of the hydroxy group in the resulting carbinol by hydrogen, and replacement of the newly introduced esterified carboxyl group by hydrogen or alkyl (e.g. by selective hydrolysis followed by the Hoffmann, Curtius or Nägeli degradation and replacement of the resulting amino group by hydrogen by treatment with nitrous acid followed by reduction of the hydroxy group, or by reduction of the corresponding acid halide group through an aldehyde and/or a hydroxymethyl group to a methyl group). In all cases the ester or nitrile obtained is, if desired, hydrolysed to the free acid, which may be converted into salts. The products are useful as medicaments or intermediates therefor. Examples describe the preparation of b -(2-naphthyl)-b -ethyl-a : a -dimethylpropionic acid and its methyl ester from 2-naphthyl ethyl ketone and from (2-naphthoyl)-dimethylacetic acid ethyl ester, each by two methods. Lists of additional starting materials and suitable reagents and solvents are given. (2 - Naphthoyl) - dimethylacetic acid ethyl ester is obtainable by refluxing 2-cyanonaphthalene with ethyl a -bromoisobutyrate in benzene in the presence of zinc. |
| priorityDate | 1948-07-30-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 41.