Acetic Acid → HCID 54163842, compound

Participants

Reaction Steps

Using the general procedure described by S. P. Bruekelman, S. E. Leach, G. D. Meakins, and M. D. Tirel (J. Chem. Soc., Perkin Trans. 1, 1984, 2801-2807), acetic acid (0.50 mL, 0.52 g, 8.7 mmol) and sodium acetate trihydrate (70 mg, 0.51 mmol) were added to a solution of 2,5-hexanedione (8.0 mL, 7.8 g, 68 mmol) and 3-bromo-4-methoxyaniline (see Y. -Y. Lui, M. Minich, J. Labelled Compounds and Radiopharmaceuticals, 1981, 18, 791-797) in 40 mL of toluene. The mixture was heated to reflux for 2 h in a flask connected to a Dean-Stark trap. After cooling the mixture to room temperature, ethyl acetate (20 mL) was added and the solution was washed with 25 mL. each of water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The organic layer was dried (sodium sulfate), decanted, and evaporated to give brown crystals. Recrystallization from 20 mL of warm hexane cooled to 0° C. yielded 8.17 g of tan crystals (67% yield). 1H NMR (400 MHz, CDCl3): δ 7.42 (d, 1H, J=2 Hz), 7.14 (dd, 1H, J=9, 2 Hz), 6.96 (d, 1H, J=9 Hz), 5.87 (s, 2H), 3.95 (s, 3H), 2.02 (s, 6H). Mass spectrum (NH3CI): m/e=280 (M+1).

Provenance & Evidence