FIELD: chemistry.
SUBSTANCE: invention relates to a method for industrial synthesis of a compound of formula (I). Method is characterised by that 7-methoxy-naphthalen-2-ol of formula (II) is introduced into the reaction, into which group -CH2-X is introduced into position 1 of the compound of formula (II), wherein X is -N(CH3)2, -CO-N(CH2-Ph)2, -CH2-OH, -CH=CH2 or -CO-NH2, to obtain a compound of formula (III), in which X is a group -N(CH3)2, -CO-N(CH2-Ph)2, -CH2-OH, -CH=CH2 or -CO-NH2. Compound of formula (III) is subjected to a sulphonylation reaction of the aromatic alcohol and substitute X of the compound of formula (III) is modified before or after the aromatic alcohol sulphonylation step using conventional chemical reactions to obtain a compound of formula (IV), in which X' is a group -CN, -CO-NH2, -CH2-OH, -CHO, -CH2-N(CH2-Ph)2, -CH2-NH-CO-CH3, -CH(OH)-CH2-OH or (2,5-dioxopyrrolidin-1-yl)methyl and R is a -CH3, - (CH2)2-CH3, -CF3 group or toluene. Compound of formula (IV) undergoes a deoxygenation reaction in the presence of a transition metal and a reducing agent to directly obtain a compound of formula (I), which is separated in form of a solid substance, if X' is a -CH2-NH-CO-CH3, or compounds of formula (V), wherein X'' is a group -CN, -CH2-N(CH2-Ph)2, -CH2-OH, -CH(OH)-CH2-OH, -CO-NH2 or (2,5-dioxopyrrolidin-1-yl) methyl. Compound of formula (V) undergoes common chemical reactions to obtain a compound of formula (I), which is isolated as a solid substance. Invention also relates to intermediate compounds and use thereof in the synthesis of agomelatine of formula (I) using said method.
EFFECT: disclosed method enables to obtain agomelatine of formula (I) with high output and excellent purity.
29 cl, 11 ex
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