Sodium Hydroxide → HCID 22018411, compound

Participants

Reaction Steps

1-{6-[(Diphenylmethylene)amino]naphthalen-2-yl}-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (15.0 g) was dissolved in THF (5 ml)-methanol (5 ml) and sodium acetate (285 mg) and hydroxylamine hydrochloride (181 mg) were added. The mixture was stirred at room temperature for 20 min. 0.1N aqueous sodium hydroxide solution was added and the mixture was extracted with ethyl acetate, washed with saturated brine and dried to give a crude product of 1-(6-aminonaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol as a pale-yellow oily substance. This product was dissolved in dichloromethane (100 ml), and pyridine (5.3 ml) and acetic anhydride (4.1 ml) were added. The mixture Was stirred at room temperature for 40 min. Saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with dichloromethane and dried. The solvent was evaporated and the residue was recrystallized from ethyl acetate to give the title compound (11.6 g) as pale-red crystals.

Provenance & Evidence