Hydrazine hydrate (1:1) → 5-(4-Methoxyphenyl)pyridazin-3(2H)-one

HRID 1186852Notes

Reaction equation

HRID 1186852 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.O.[NH2:17][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][NH:17][C:5](=[O:6])[CH:4]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 596519785-Hydroxy-4-(4-methoxy-phenyl)-5H-furan-2-one

Product 1

HCID 135589165-(4-Methoxyphenyl)pyridazin-3(2H)-oneYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 5-hydroxy-4-(4-methoxyphenyl)-5H-furan-2-one (2.00 g, 9.7 mmol) in 15 mL of ethanol was stirred as hydrazine hydrate (0.97 g, 2.0 eq) was added in dropwise. The reaction was stirred at 85° C. overnight, and then the solvent was reduced. The solid was collected and washed with cold EtOH to give 1.7 g (87%) of 5-(4-methoxy-phenyl)-2H-pyridazin-3-one: MS m/z 203 (M+H).

Workup

  1. additionwas added in dropwise
  2. customThe solid was collected
  3. washwashed with cold EtOH

Sources & evidence

ORD record
ord-6da63d5897cd488cb4ad67bf98e739fc
Source dataset
uspto-grants-2014_03
Patent number
US08673916B2

Reaction notes

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