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

HRID 1244260Notes

Reaction equation

HRID 1244260 reaction equation
[NH2:1][NH2:2].O.[C:4]([CH:7]([CH2:12][CH2:13][CH3:14])[CH2:8][C:9](O)=[O:10])(=O)[CH3:5]>CCO>[CH3:5][C:4]1[CH:7]([CH2:12][CH2:13][CH3:14])[CH2:8][C:9](=[O:10])[NH:1][N:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 219192833-Acetyl-hexanoic acid

Product 1

HCID 219192746-Methyl-5-propyl-4,5-dihydropyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

NH2NH2—H2O (6.94 ml, 143 mmol) is added to a solution of 3-acetyl-hexanoic acid (18.8 g, 119 mmol) in EtOH (150 ml), and the mixture is refluxed (oil bath 85° C.) for 4 hours. The solvent is removed in vacuo and water (100 ml) and EtOAc (100 ml) are added to the residue. The layers are separated and the aqueous layer is extracted with EtOAc (3×100ml). The combined extracts are washed with brine (150 ml), dried (Na2SO4) and evaporated. 6-methyl-5propyl-4,5-dihydropyridazin-3-one is obtained as a light yellow oil, and is used in the next step.

Workup

  1. customThe solvent is removed in vacuo and water (100 ml) and EtOAc (100 ml)
  2. additionare added to the residue
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (3×100ml)
  5. washThe combined extracts are washed with brine (150 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-d7a20aba0c274203b2a8b46e4290b807
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

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