Bromine → 6-Methyl-5-propylpyridazin-3(2H)-one

HRID 1244261Notes

Reaction equation

HRID 1244261 reaction equation
[CH3:1][C:2]1[CH:3]([CH2:9][CH2:10][CH3:11])[CH2:4][C:5](=[O:8])[NH:6][N:7]=1.BrBr>CC(O)=O>[CH3:1][C:2]1[C:3]([CH2:9][CH2:10][CH3:11])=[CH:4][C:5](=[O:8])[NH:6][N:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 219192746-Methyl-5-propyl-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 219192926-Methyl-5-propylpyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 6-methyl-5-propyl-4,5-dihydropyridazin-3-one (16.7 g, 108 mmol) in HOAc (200 ml) heated to 85° C. is added Br2 (5.5 ml, 108 mmol) dropwise. After the addition, the mixture is stirred at 85° C. for 1 hour. The solvent is removed in vacuo and the residue is dissolved in EtOAc (250 ml) and washed with NaHCO3 (200 ml), followed by Na2S2O3 saturated solution (50 ml) and brine (200 ml). The organic phase is dried (Na2SO4) and evaporated. The resulting 6-methyl-5-propyl-pyridazin-3-one is obtained as a yellow solid, which is used in the next step without further purification.

Workup

  1. additionAfter the addition
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in EtOAc (250 ml)
  4. washwashed with NaHCO3 (200 ml)
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-0dee976c96ec4fe197e742dd4a1fa4b6
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

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