Patent ES-265741-A1 (ES)
Title: Amides and process for their preparation
IPC: C07D213/74
Filed: 1961-03-14
Abstract: The invention comprises compounds of the formula <FORM:0912496/IV (b)/1> (wherein Z is one or more hydrogen atoms, or lower alkyl, amino or lower alkylamino groups R1 and R2 are hydrogen or lower alkyl and R3 is lower alkyl or lower alkoxy, the word "lower" referring to groups containing at most 4 carbon atoms) and their non-toxic acid-addition salts and their preparation by condensing a compound of the formula <FORM:0912496/IV (b)/2> (hereinafter referred to as Py-CH(R1)-X) with a compound of the formula <FORM:0912496/IV (b)/3> (hereinafter referred to as B-CO-Y) wherein (1) X is -NHR2 and Y is halogen, hydroxyl, azido, phenylthio, p-nitrophenylthio, OR1, OCOOR1 or OCOR1 wherein R1 is a possibly hindered alkyl group, a 1-imidazolyl group, -OCH2CN or OC(=CH2)OR1 and wherein when Y is OH the reaction can be carried out with the dialkylchlorophosphite, pyrophosphite, dialkylchloroarsenite or carbodiimide derivative or (2) X is halogen, a quaternary ammonium group or an alkyl or arylsulphonate group and Y is -NHR2 and the metal salt of the amide is used (optionally when X is halogen) or (3) X is a group of the structure <FORM:0912496/IV (b)/4> and Y is OH. Examples are given. Acid halides B-CO-Hal are prepared from the acid and phosphorus oxychloride or other halogenating agents. Acid azides B-CO-N3 are prepared from the acid and hydrazine to give the hydrazide B-CO-NHNH2 which is then treated with nitrous acid. Acid anhydrides B-CO-O-CO-R1 are prepared from BCOOH and R1COCl. Compounds B-CO-O-CO-OR1 are prepared from BCOOH and R1OCOCl. Phosphorus p derivatives BCOOP(OC2H5)2 are prepared from BCOOH and (C2H5O)2BCl or (C2H5O)2POP(OC2H5)2. Arsenic derivatives BCOOA5(OC2H5)2 are prepared from BCOOH and (C2H5O)2A5Cl. Imidazole derivatives B-CO-(1-imidazolyl) are prepared from BCOOH and di-imidazolyl ketone. Cyanoesters BCOOCH2CN are prepared from the triethylammonium salt of the acid and chloroacetonitrile. Pyridine derivatives Py-N(R2)-P(OC2H5)2 are prepared from Py-N(R2)-H and (C2H5O)PCl or (C2H5O)2POP(OC2H5)2 and Py-N(R2)-P=N-Py are prepared from Py-N(R2)H anl PCl3. 2-Amino - 3 - aminomethyl-6-methyl-pyridine hydrochloride is prepared by hydrogenation of 2 - amino - 6 - methyl-nicotinonitrile. 3-Aminomethyl - 2 - n - butylamino-6-methyl-pyridine hydrochloride, 4 - aminomethyl - 2 - methylpyridine dihydrochloride, 3-aminomethyl-2-methylamino-6-methyl-pyridine dihydrochloride and 2-amino-3-aminomethyl-pyridine dihydrochloride are prepared similarly. 5 - Amino - 3 - aminomethyl-4,6-dimethylpyridine dihydrochloride monohydrate is prepared by reduction of 2-chloro-4,6-dimethyl-5-nitro-nicotinonitrile. 2 - n - Butylamino-6-methyl-nicotinonitrile is prepared from 2 - chloro-6-methyl-nicotinonitrile and n-butylamine. 3-Aminomethyl - 6 - (methyl and ethyl)-pyridine dihydrochlorides are prepared by reduction of 2-chloro-6-(methyl and ethyl)-nicotinonitriles. 3 - Methylaminomethyl - pyridine dihydrochloride is prepared by reacting 3-amino-methylpyridine with tosyl chloride to give N - (3 - pyridylmethyl)-p-toluenesulphonamide, reacting this with dimethyl sulphate to give N - methyl - N - (3 - pyridylmethyl)-p-toluene-sulphonamide and hydrolysing this.