Sodium borohydride → 10-Methyl-8,9,10,11-tetrahydropyridazino[1',6':1,2]imidazo[4,5-c]quinoline

Participants

Reaction Steps

A solution of 10-methyl-8,9-dihydropyridazino[1′,6′:1,2]imidazo[4,5-c]quinoline (1.96 g, 8.30 mmol) in methanol (50 mL) was cooled to 0° C. The solution was treated with NaBH4 (1.26 g, 33.2 mmol) over 3 min. The reaction was allowed to come to ambient temperature over 3 h. The reaction was quenched with slow addition of saturated NH4Cl aqueous solution (20 mL) and then concentrated under reduced pressure to remove the methanol. The residual material was partitioned between chloroform (75 mL) and 10% Na2CO3 aqueous solution (25 mL) and then separated. The organic portion was washed with water (25 mL) and brine (25 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a tan solid. Purification by column chromatography (100 g silica gel eluted with 95:5 chloroform:methanol) yielded 1.56 g of 10-methyl-8,9,10,11-tetrahydropyridazino[1′,6′:1,2]imidazo[4,5-c]quinoline as a tan solid.

Provenance & Evidence