Acetic Acid → 4-{(E)-2-[3-(3-Chlorophenyl)-1H-pyrazol-5-yl]ethenyl}phenol

Participants

Reaction Conditions

Reaction Steps

Hydrazine dihydro-chloride (0.263 g, 2.50 mmol) was added to a sealed tube charged with (2Z,4E)-1-(3-chlorophenyl)-3-hydroxy-5-(4-hydroxyphenyl)penta-2,4-dien-1-one (0.717 g, 2.39 mmol) in absolute ethanol (8 mL) and a catalytic amount of acetic acid. The reaction tube was sealed and heated to 80° C. After 12 hours the reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in a small amount of methanol and precipitated with water, and the solid was collected by vacuum filtration to provide the title compound in (288 mg, 41% yield) as a yellow solid: 1H NMR (400 MHz, CD3OD): δ 7.79 (bs, 1H), 7.68 (bd, J=7.6 Hz, 1H), 7.37 (m, 3H), 7.29 (bd, J=7.6 Hz, 1H), 7.12 (d, J=16.4 Hz, 1H), 6.86 (d, J=16.4 Hz, 1H), 6.81 (bs, 1H), 6.77 (m, 2H); MS (EI) for C17H13 ClN2O: 297.1 (MH+).

Provenance & Evidence