Methylhydrazine → 4-Bromo-1,2-dihydro-1-methyl-3,6-pyridazinedione

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Reaction Steps

To a solution of 3-bromofuran-2,5-dione (100 g, 0.565 mol) in HOAc (1.0 L) cooled in an ice-water bath, 40% aq. methylhydrazine solution (65 g, 0.565 mol) was added dropwise while the internal temperature was held below 20° C. The mixture was allowed to warm to room temperature and stirred for 16 h. The precipitated solid was collected by filtration, washed with EtOAc, and dried in vacuo to give desired product as a white solid: LC/MS m/z=206.9 (M+H)+; 1H NMR (400 MHz, CD3OD) δ: 7.35 (s, 1 H), 3.60 (s, 3 H).

Provenance & Evidence