Methylhydrazine → HCID 59260113, compound

Participants

Reaction Steps

The mixture of 4-iodoacetophenone (1.00 g, 4.06 mmol) and glyoxalic acid monohydrate (0.45 g, 4.9 mmol) in 20 mL acetic acid was refluxed for 18 hrs before concentrated in vacuo. The dry residue was then stirred in 15 mL water to form a slurry material. To it was added carefully with ammonium hydroxide (30%) until pH 9 as indicated by pH paper. The pH was critical for this reaction. Methylhydrazine (0.43 mL) was added, and the reaction was sent to 100° C. bath for 3 hrs before the mixture was diluted with ethyl acetate. The organic phase was washed with brine, dried, concentrated in vacuo, and purified by flash column using 5% methanol in DCM isocratically to yield 6-(4-iodophenyl)-2-methylpyridazin-3(2H)-one (680 mg, 54%). MS found for C11H91N2O (M+H)+ 313.0.

Provenance & Evidence