Sodium Hydroxide → HCID 86612243, compound

Participants

Reaction Steps

Methoxylamine hydrochloride (3.39 g, 40.6 mmol, 2 eq) and 6M sodium hydroxide solution (7.5 mL, 44.7 mmol. 2.2 eq) were added sequentially to a solution of 4-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyraldehyde (5.73 g, 20.3 mmol, 1 eq) in methanol (80 mL) and stirred overnight. The mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (100 mL) and water (60 mL). The pH of the mixture was adjusted to 7 and the layers were separated. The aqueous layer was extracted with dichloromethane (2×20 mL) and the combined organics were washed with brine (75 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 6.45 g of 4-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyraldehyde O-methyloxime as an orange oil with an E/Z ratio of 77:23. The material was used in subsequent steps without any further purification.

Provenance & Evidence