Potassium Carbonate → 4-(4-Pyridinylmethoxy)-1-naphthalenamine

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Reaction Steps

4-tert-Butyloxycarbonylamino-1-naphthol (41) can be alkylated with 4-chloromethylpyridine hydrochloride in a non-protic solvent, such as acetonitrile, with a base, such as powdered potassium carbonate, at temperatures between 60-80° C. Purification of the product 4-tert-butyloxycarbonylamino-1-(pyridin-4-yl-methyl)naphthalene (44) can be accomplished by silica gel chromatography. Removal of the BOC-protecting group can be accomplished with HCl in a non-protic solvent, such as dioxane, to provide 1-amino-4-(pyridin-4-yl-methoxy)naphthalene (43) as the hydrochloride salt.

Provenance & Evidence