alpha-Hydrazino-m-cresol dihydrochloride → 6-(3,5-Dibromo-4-hydroxyphenyl)-2-(3-hydroxybenzyl)-4,5-dihydropyridazin-3(2H)-one

Participants

Reaction Steps

A stirred mixture of 4-(3,5-dibromo-4-hydroxyphenyl)-4-oxobutanoic acid (H) (150 mg, 0.426 mmol) and 3-hydroxybenzylhydrazine dihydrochloride (135 mg, 0.639 mmol) in ethanol was heated to reflux. After heating for 16 h, the reaction mixture was cooled down and the precipitate formed was collected and dried in vacuo. This gave the title compound as a red solid (95 mg, 49%)1H NMR δ (ppm) (DMSO-d6): 2.59 (2 H, t), 3.01 (2 H, t, J=8.2 Hz), 4.88 (2H, s), 6.67 (1 H, d, J=8.2 Hz), 6.69-6.76 (2 H, m), 7.14 (1 H, t, J=7.8 Hz), 7.92 (2 H, s), 9.39 (1 H, s), 10.44 (1 H, s). LCMS (10 cm_apci_formic) Rt 3.33 min; m/z 453/455/457 [M+H].

Provenance & Evidence