Hydrazine hydrate (1:1) → 4-Methyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one

HRID 1425720Notes

Reaction equation

HRID 1425720 reaction equation
[CH3:1][CH:2]([CH2:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3](O)=[O:4].O.[NH2:16][NH2:17]>C(O)C>[CH3:1][CH:2]1[CH2:6][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:17][NH:16][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 744922-Methyl-4-oxo-4-phenylbutanoic acid

Product 1

HCID 139013904-Methyl-6-phenyl-4,5-dihydropyridazin-3(2H)-oneYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

7.7 g (40 mmole) of 2-methyl-4-oxo-4-phenylbutanoic acid was added to a 100 ml single-necked round bottom flask followed by 3.0 ml (60 mmole) of hydrazine monohydrate and then 20 ml of reagent grade ethanol (100%, 95% of ethanol should be fine also). The flask was fitted with a reflux condenser and the reaction mixture was heated to reflux in an oil bath at 110 C (temperature of oil bath) and stirred for 2 h. The flask was then removed from the oil bath and the reaction mixture cooled to ambient temperature. The stir bar was removed and the solvent was evaporated in vacuo in a water bath at 45° C. The residue was then treated with 50 ml of Milli-Q water and stirred for 10 minutes to give a suspension. The precipitate was collected by filtering, washed with 100 ml of 2N NaHCO3, then washed with 60 ml Milli-Q water three times, and dried over a medium frit sintered glass funnel in vacuo to give 7.15 g of white crystals (Syn. ID, WH-8-004). Yield, 95%, confirmed by ESI-MS. ESI-MS: m/z 189.2 (M+H+).

Workup

  1. customThe flask was fitted with a reflux condenser
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux in an oil bath at 110 C (temperature of oil bath)
  4. customThe flask was then removed from the oil bath
  5. customThe stir bar was removed
  6. customthe solvent was evaporated in vacuo in a water bath at 45° C
  7. additionThe residue was then treated with 50 ml of Milli-Q water
  8. stirringstirred for 10 minutes
  9. customto give a suspension
  10. customThe precipitate was collected
  11. filtrationby filtering
  12. washwashed with 100 ml of 2N NaHCO3
  13. washwashed with 60 ml Milli-Q water three times
  14. customdried over a medium frit sintered glass funnel in vacuo

Sources & evidence

ORD record
ord-47a6d120410d474d81edef2debfcf692
Source dataset
uspto-grants-2015_01
Patent number
US08933076B2

Reaction notes

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