Hydrazine → 6-(4-Methoxyphenyl)-2,3-dihydropyridazin-3-one

HRID 1990773Notes

Reaction equation

HRID 1990773 reaction equation
[NH2:1][NH2:2].O[CH:4]([CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=O)[C:5](OCC)=[O:6]>C(O)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[N:2]=[N:1][C:5]([OH:6])=[CH:4][CH:10]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 23153694Ethyl 2-hydroxy-4-(4-methoxyphenyl)-4-oxobutanoate

Product 1

HCID 28101666-(4-Methoxyphenyl)-2,3-dihydropyridazin-3-oneYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4.91 ml (98.0 mmol) of hydrazine was added to an ethanol solution (50 ml) of 20.62 g (82.0 mmol) of the obtained ethyl 2-hydroxy-4-(4-methoxyphenyl)-4-oxo-butyrate, and the reaction liquid was stirred at 60° C. for 4 h ours. The reaction liquid was concentrated under reduced pressure, and the resulting solid was washed with diethyl ether to obtain 16.18 g (yield: 80%) of 6-(4-methoxyphenyl)-pyridazin-3-ol as a white solid.

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. washthe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-8ffe7e6c3eb94d889afc3a3446075601
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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