Nitric Acid → HCID 178468352, compound

Participants

Reaction Conditions

Reaction Steps

4-Morpholin-4-ylaniline (653 mg, 3.67 mmol) was added to a mixture of 3 mL of phosphoric acid (85%) and 2 mL of nitric acid (65%) at −6° C. When the resulting mixture reached to room temperature, it was cooled to −6° C. and sodium nitrite (253 mg, 3.67 mmol) was added during 10 min. Small piece of ice (50 g) was added into the solution. The mixture was added at 0° C. to a suspension of 2,4-pentanedione (367 mg, 3.67 mmol) and potassium acetate (20 g) in ethanol (250 mL). The solution was stirred for 15 min, and then added to 250 mL of saturated Na2CO3 aqueous solution, extracted with dichloromethane, washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the title compound (870 mg, 82% yield) as a brown solid: 1H NMR (400. MHz, CDCl3): δ 2.50 (3H, s), 2.61 (3H, s), 3.15-3.18 (4H, m), 3.80-3.83 (4H, m), 6.98-7.03 (2H, m), 7.45-7.50 (2H, m), 14.37 (1H, s).

Provenance & Evidence