合成路线1

The reaction of 3-chloro-4-nitrobenzoic acid (I) with methylamine gives 3-(methylamino)-4-nitrobenzoic acid (II), which is hydrogenated in the presence of Raney Nickel to yield 4-amino-3-(methylamino)benzoic acid (III). Treatment of compound (III) with sodium nitrite affords 1-methyl-1H-benzotriazole-6-carboxylic acid (IV), which is reduced with lithium aluminum hydride in THF to give 6-(hydroxymethyl)-1-methyl-1H-benzotriazole (V). Oxidation of (V) with potassium permanganate in dichloroethane yields 1-methyl-1H-benzotriazole-6-carboxaldehyde (VI), which on treatment with the Grignard reagent derived from 1-bromo-4-chlorobenzene (VII) gives 6-(4-chloro-alpha-hydroxybenzyl)-1-methyl-1H-benzotriazole (VIII). Treatment of compound (VIII) with thionyl chloride in THF yields 6-(alpha,4-dichlorobenzyl)-1-methyl-1H-benzotriazole (IX), which is finally condensed with 1,2,4-triazole (X) and sodium hydride in DMF.