Ammonium formate → HCID 22602609, compound

Participants

Reaction Conditions

Reaction Steps

5-Nitroboronophthalide (2.72 g, 15.2 mmol) and 10% palladium on carbon (911 mg) are suspended in 30 mL of anhydrous tetrahydrofuran. Ammonium formate (4.41 g, 70 mmol) is added and the mixture is stirred at 50° C., under nitrogen for 3 hr. After cooling to room temperature, the catalyst is removed by filtration through a pad of Celite, which is then washed with ˜30 mL of methanol. Concentration in vacuo gives a light brown oil that is purified by dissolution in ethyl acetate and filtration through a plug of silica. Recrystallization from ethanol and water gives a light yellow crystalline solid (1.12 g, 7.52 mmol, 49.5%) with a m.p. of 160-161° C.

Provenance & Evidence