Patent GB-998524-A (GB)
Title: Naphthalene derivatives
Inventor: MCLOUGHLIN BERNARD JOSEPH
Filed: 1962-01-29
Abstract: The invention comprises compounds (b -adrenergic blocking agents) of the general formula <FORM:0998524/C2/1> wherein R1 stands for a hydrogen atom or an alkyl radical, R2 stands for a hydrogen atom or an alkyl radical, R3 stands for an alkyl, hydroxyalkyl or aralkyl radical and the naphthalene nucleus may optionally bear one or more halogens, alkoxy, alkyl or alkylene substituents, and the acid addition salts thereof, provided that R2 and R3 do not stand for the same alkyl radical at the same time, and excluding 1-(1-naphthyl) - 2 - methylamino - 1 - propanol and the acid addition salts thereof, and their preparation by (a) reducing a compound of the formula <FORM:0998524/C2/2> (wherein X stands for a halogen atom and the naphthalene nucleus may optionally be substituted) and reacting the product with NHR2R3, (b) reacting a compound of the formula <FORM:0998524/C2/3> (wherein R stands for the group <FORM:0998524/C2/4> or -CHOH.CHR1X and the naphthalene nucleus may optionally be substituted) with NHR2R3, (c) reducing a compound of the formula <FORM:0998524/C2/5> (wherein the naphthalene nucleus may optionally be substituted) or an acid addition salt thereof, (d)-in cases where R2 stands for a hydrogen atom and R3 stands for a radical of the formula -CHR4R5(wherein R4 stands for a hydrogen atom or an alkyl radical and R5 stands for an alkyl, aryl or aralkyl radical)-reacting a compound of the formula <FORM:0998524/C2/6> (wherein A stands for the group CO or CHOH and the naphthalene nucleus may optionally be substituted), optionally generated in situ, with R4COR5 under reducing conditions, or (e)-in cases where R1 stands for a hydrogen atom-reducing a compound of the formula <FORM:0998524/C2/7> (wherein R6 stands for an aldehyde radical or a radical of the formula -CH(OR7)OR8, wherein R7 and R8 are the same or different and stand for hydrogen atoms or alkyl radicals containing not more than five carbon atoms, and the naphthalene nucleus may optionally be substituted) in the presence of NHR2R3 or an acid addition salt thereof, optionally followed in each case by acid addition salt formation.  The following intermediates are prepared from the starting materials indicated in parentheses: 4 - methyl - 1 - naphthacyl bromide (4-methyl - 1 - acetylnaphthalene); 1 - (isobutylaminoacetyl)naphthalene and its hydrochloride (1-naphthacyl bromide and isobutylamine); 1 - (hydroxyiminoacetyl)naphthalene (1 - acetyl-naphthalene and amyl nitrite); 5-acenaphthenyl-glyoxal (5 - acetylacenaphthene); 1 - t. - butylaminoacetyl - 4 - methylnaphthalene (4 - methyl - 1 - naphthacyl bromide and t. - butylamine); 4 - chloro - 1 - naphthylglyoxal (1 - acetyl - 4 - chloronaphthalene); 1 - (4 - methoxy - 1 - naphthyl) - 2 - chloroethanol (4 - methoxy - 1 - naphthacyl chloride); 4-methoxy-1-isopropylaminoacetylnaphthalene (4 - methoxy - 1 - naphthacyl iodide and isopropylamine); 1-(1-naphthyl)-2-aminoethanol (1 - aminoacetylnaphthalene hydrochloride); 1 - (a  - hydroxyiminopropionyl) naphthalene (ethyl 1 - naphthyl ketone and amyl nitrite); 2 - methoxy - 1 - naphthylglyoxal (1 - acetyl - 2 - methoxynaphthalene).