2-Bromoacetamidopyridine → 2-Chloro-1-(2-oxo-2-(2-pyridyl)ethyl)naphtho[2,3-d]imidazole

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Reaction Steps

In a manner analogous to Example 28 steps a)→d) 2-chloro-1H-naphtho[2,3-d]imidazole (7.5 g) was reacted with 2-bromoacetylpyridine (8.7 g) to give 2-chloro-1-(2-oxo-2-(2-pyridyl)ethyl)naphtho[2,3-d]imidazole (9 g). This was reacted with thiourea (5.5 g) then NH4OH solution (100 ml) to give 2-mercapto-1-(2-oxo-2-(2-pyridyl)ethyl)naphtho[2,3-d]imidazole which compound was reduced with NaBH4 to give 2-mercapto-1-(2-hydroxy-2-(2-pyridyl)ethyl)naphtho[2,3-a]imidazole (1.3 g). Treatment of this with polyphosphoric acid (23 g) gave the title compound (0.75 g.) mp 197.5°-198.5° C.

Provenance & Evidence