Metal complex dyes based on Bucherer naphthols

A compound of formula (1-6)

• wherein
• B is a direct bond or a bridge member;
• X is a fiber-reactive structural element;
• W1 is vinyl or a group of the formula —CH2—CH2—V, where V is an alkali-eliminable radical;
• R1 and R2 are independently hydrogen, chlorine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, carboxyl, sulfamoyl, hydroxyl or sulfo;
• R3 is hydrogen, hydroxyl, carboxyl or sulfo;
• R4 is hydrogen or sulfo;
• R5 is hydrogen, alkyl of 1 to 4 carbon atoms which can be substituted by halogen, hydroxyl, cyano, alkoxy of 1 to 4 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, carboxyl, sulfo or sulfato;
• h, k, l and m are independently 0 or 1;
• M is hydrogen, an alkali metal, or the mole equivalent of an alkaline earth metal.

A compound of the formula (3)

• wherein
• B is a direct bond or a bridge member;
• W1 is vinyl or a group of the formula —CH2—CH2—V, where V is an alkali-eliminable radical;
• R1 and R2 are independently hydrogen, chlorine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, carboxyl, sulfamoyl, hydroxyl or sulfo;
• R3 is hydrogen, hydroxyl, carboxyl or sulfo;
• R4 is hydrogen or sulfo;
• R5 is hydrogen, alkyl of 1 to 4 carbon atoms which can be substituted by halogen, hydroxyl, cyano, alkoxy of 1 to 4 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, carboxyl, sulfo or sulfato;
• h, k, l and m are independently 0 or 1;
• Me is copper, cobalt or chromium;
• M is hydrogen, an alkali metal, or the mole equivalent of an alkaline earth metal.

A process for preparing compounds of the general formula (3) starting from amino compounds of the general formula (8a) or (8b)

• wherein
• L is a hydrolyzable protecting group and
• B is a direct bond or a bridge member;
• R1 is hydrogen, chlorine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, carboxyl, sulfamoyl, hydroxyl or sulfo;
• R5 is hydrogen, alkyl of 1 to 4 carbon atoms which can be substituted by halogen, hydroxyl, cyano, alkoxy of 1 to 4 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, carboxyl, sulfo or sulfato;
• K is 0 or 1;
• M is hydrogen, an alkali metal, or the mole equivalent of an alkaline earth metal, by diazotization and coupling onto a compound of the formula (1-3)
• wherein
• W1 is vinyl or a group of the formula —CH2—CH2—V, where V is an alkali-eliminable radical;
• R2 is hydrogen, chlorine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, carboxyl, sulfamoyl, hydroxyl or sulfo;
• R3 is hydrogen, hydroxyl, carboxyl or sulfo;
• R4 is hydrogen or sulfo;
• l and m are independently 0 or 1;
• and subsequent reaction with copper, cobalt or chromium donors and subsequent hydrolysis of the protected amino group, or reduction of the nitro group.