1-Chlorophenyl-2-methanol is dissolved in dimethylformamide; NaH is added
and the mixture is stirred at 20°C for 1 h. After a solution of 4-chloro-1-
methyl-1H-imidazo[4,5-c]pyridine [melting point 132°-134°C; obtainable by
reaction of 4-methylamino-3-nitropyridine with HCl/SnCl2 to give 3-amino-2-
chloro-4-methylaminopyridine (melting point 170°-173°C) and reaction with
HCOOH/acetic anhydride] in dimethylformamide has been added, the mixture
is stirred at 90°-95°C for 15 h. The mixture is evaporated and the residue is
worked up in the customary manner to give 4-o-chlorobenzyloxy-1-methyl-
1H-imidazo[4,5-c]pyridine, melting point 132°-135°C (crystallize from ethyl
acetate-tetrahydofuran).
