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

HRID 898694Notes

Reaction equation

HRID 898694 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 yellow solid is used in 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
  7. customThe resulting yellow solid is used in next step without further purification

Sources & evidence

ORD record
ord-be1966c2107a4fd2afe5505c9a173e62
Source dataset
uspto-grants-2008_04
Patent number
US07351826B2

Reaction notes

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