Reaction #955928

Reaction equation

hydrazine

glyoxylic acid monohydrate

2′,4′-dimethylacetophenone

NH4OH

→

desired product

Yield 55.0%

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

Yield 55.0%

Solvents

water

Conditions

Workup

1. 1
   TemperatureThen the mixture was cooled down to room temperature
2. 2
   WashThe mixture was washed with DCM
3. 3
   Temperaturethe solution was refluxed for 3 hours
4. 4
   TemperatureAfter cooling to room temperature the precipitate
5. 5
   Filtrationwas collected by filtration

Procedure

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