Réaction #955928

Équation de réaction

hydrazine

glyoxylic acid monohydrate

2′,4′-dimethylacetophenone

NH4OH

→

desired product

Rendement 55.0%

6-(2,4-dimethylphenyl)pyridazin-3(2H)-one

Rendement 55.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   TempératureThen the mixture was cooled down to room temperature
2. 2
   LavageThe mixture was washed with DCM
3. 3
   Températurethe solution was refluxed for 3 hours
4. 4
   TempératureAfter cooling to room temperature the precipitate
5. 5
   Filtrationwas collected by filtration

Mode opératoire

A mixture of glyoxylic acid monohydrate (920 mg, 10 mmol) and 2′,4′-dimethylacetophenone (4.45 mL, 30 mmol) was stirred at 150° C. for 2 hr. Then the mixture was cooled down to room temperature and water (4 mL) was added followed by conc. aq. NH4OH (1 mL). The mixture was washed with DCM. To the ammoniac solution was added hydrazine (314 μL, 10 mmol) and the solution was refluxed for 3 hours. After cooling to room temperature the precipitate was collected by filtration to give the desired product as a white powder (1.1 g, 55%), 1H NMR (300 MHz, dMSO): δ 2.22 (s, 3H), 2.25 (s, 3H), 6.93-6.95 (d, 1H), 7.15 (m, 3H), 7.21-7.23 (d, 1H), 7.57-7.61 (d, 1H), 13.1 (bs, 1H); (M+H, 201).

Source