Reacción #955928

Ecuación de reacción

hydrazine

glyoxylic acid monohydrate

2′,4′-dimethylacetophenone

NH4OH

→

desired product

Rendimiento 55.0%

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

Rendimiento 55.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThen the mixture was cooled down to room temperature
2. 2
   LavadoThe mixture was washed with DCM
3. 3
   Temperaturathe solution was refluxed for 3 hours
4. 4
   TemperaturaAfter cooling to room temperature the precipitate
5. 5
   Filtraciónwas collected by filtration

Procedimiento

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).

Fuente