GB1354098A - 1-hydroxyiminonaphthalene derivatives - Google Patents

Abstract

1354098 1-Hydroxylimino-1,2-dihydronaphthalenes TEIKOKU HORMONE MFG CO Ltd 23 April 1971 [24 April 1970 (3) 30 Jan 1971 16 March 1971 19 March 1971 20 March 1971 (2) 20 April 1971] 41047/73 Divided out of 1354097 Heading C2C Novel 1-hydroxylimino-1,2-dihydronaphthalenes of the general formula wherein ring A is optionally substituted; ring B optionally contains a 3,4-double bond; and R is a methyl, hydroxymethyl, alkoxymethyl, alkoxyalkoxymethyl, (optionally substituted amino)alkoxymethyl, halomethyl, (optionally substituted amino)methyl or cyano group, or a group of the formula -C(=Y)R1, in which R1 is a hydroxyl, optionally substituted amino, C 1-12 hydrocarbyl, optionally nitro- or (C 1-4 alkoxy)-substituted C 1-12 hydrocarbyloxy, -OM1/12 (M is an alkali, alkaline earth or Al atom, an ammonium group or an organic base cation and n is the valency of M) or -O(AlOH)¢ group and Y is O or S, Y being O when R 1 is a hydroxyl, hydrocarbyloxy or -OM1/12 group, and acid addition salts thereof are prepared (a) by reacting a 1-oxo-1,2-dihydronaphthalene of the general formula with hydroxylamine or a salt thereof; (b) when ring B contains no 3,4-double bond in ring B, by hydrogenating the corresponding compound in which ring B contains a 3,4-double bond; and (c) when ring B contains a 3,4-double bond, by dehydrogenating the corresponding compound in which ring B contains no 3,4-double bond; and optionally salifying a free base product with an acid. 1-Oxo-1,2-dihydronaphthalenes of the second general formula above wherein ring B contains no 3,4-double bond are prepared by reacting a 1-tetralone of the general formula with an ester of the general formula RCOOR<SP>1</SP>, wherein R<SP>1</SP> is a C 1-4 alkyl group, in the presence of NaH of an alkali metal alcoholate at 0-80‹C.; or, when a nitro substituent is present, by nitrating the corresponding unsubstituted compound.