Methylhydrazine → 5-(4-methoxy-phenyl)-2-methyl-2H-pyridazin-3-one

HRID 2042555Notes

Reaction equation

HRID 2042555 reaction equation
O[CH:2]1[O:6][C:5](=O)[CH:4]=[C:3]1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.[CH3:16][NH:17][NH2:18]>C(O)C>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:2]=[N:18][N:17]([CH3:16])[C:5](=[O:6])[CH:4]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 596519785-Hydroxy-4-(4-methoxy-phenyl)-5H-furan-2-one

Product 1

HCID 569461985-(4-methoxy-phenyl)-2-methyl-2H-pyridazin-3-oneYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 5-hydroxy-4-(4-methoxyphenyl)-5H-furan-2-one (2.06 g, 10 mmol) in 30 mL of ethanol was stirred as methylhydrazine (0.78 mL, 1.5 eq) was added dropwise. The reaction was heated to reflux at 85° C. for 2 h, then the solvent was reduced at reduced pressure to give a solid, which was collected and washed with cold EtOH to give 1.0 g (46%) of 5-(4-methoxy-phenyl)-2-methyl-2H-pyridazin-3-one: MS m/z 217 (M+H).

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction was heated
  3. customto give a solid, which
  4. customwas collected
  5. washwashed with cold EtOH

Sources & evidence

ORD record
ord-96249b385c9c4f3c8f41388759d4390c
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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