http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-567611-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_f3d60eba74b824f1468a25815ed6b1ec |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D213-85 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D213-73 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D213-67 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D213-67 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D213-73 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D213-85 |
| filingDate | 1942-11-20-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1945-02-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-567611-A |
| titleOfInvention | Improvements in or relating to the production of 3-4-di(aminomethyl)-5-amino-6-methyl pyridine and to the production of vitamin b therefrom |
| abstract | 3,4 - Di - (aminomethyl) - 5 - amino - 6 - methyl pyridine, which on deamination (replacement of -NH2 by -OH) yields vitamin B6, is prepared by reducing 2 - halo - 3,4 - dicyano - 5 - amino - 6 - methyl pyridine. An ester of 3-cyano-4-carboxy - 6 methyl - pyridone - 2 is reacted with ammonia to form the amide, this is dehydrated to 3,4-dicyano-6-methyl-pyridone-2, the latter nitrated to yield the 5-nitro derivative which on halogenation gives 2 - halo - 3,4 - dicyano - 5 - nitro-6-methyl-pyridine yielding on reduction first the corresponding 5-amino compound and then 3,4 - di - (aminomethyl) - 5 - amino - 6 - methyl pyridine. Deamination gives vitamin B6-3,4 - di - (hydroxymethyl) - 5 - hydroxy - 6 - methyl pyridine. In an example, the ethyl ester of 3 - cyano - 4 - carboxy - 6 - methyl - pyridine - 2 is added to methanol saturated with ammonia at 0 DEG C., and the amide isolated by concentrating in vacuo. Other alkyl, aromatic or aralkyl esters may be used, or esters derived from cycloaliphatic, heterocyclic or nitro alcohols, e.g. 2-nitro-2-methyl-1-propanol. Dehydration of the amide is effected with phosphorus oxychloride at 145-150 DEG C. or, in the presence of toluene, at a lower temperature. Other dehydrating agents and solvents may be used. The dicyano compound is nitrated in acetic anhydride at 45-52 DEG C. with fuming nitric acid and a little urea. Halogenation is effected with PCl5 in chlorbenzene at 135 DEG C. Other halogenating agents, e.g. PBr5 may be used. Reduction of the nitro group is carried out with hydrogen using platinum oxide as catalyst and acetic anhydride as solvent. Other catalysts or acid and metals or alkaline reduction may, however, be employed. A solution of the 2-chlor - 3,4 - dicyano - 5 - amino - 6 - methyl pyridine and HCl in aqueous methanol is added to a methanol suspension of reduced palladium chloride while absorbing hydrogen at 30 DEG C. The trihydrochloride of 3,4-di-(aminomethyl)-5-amino-6-methyl pyridine is obtained. Using HBr, the trihydrobromide can be obtained similarly. An aqueous solution of the hydrochloride is added with NaNO2 solution to hot hydrochloric acid, the product evaporated to dryness in vacuo, and extracted with acetone. The residue is extracted with ethanol and the extract worked up to isolate vitamin B6. Other nitrites, e.g. KNO2, or amyl nitrite may alternatively be used. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-2860141-A |
| priorityDate | 1941-09-26-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 60.