Bromine → 6-Isopropyl-3-pyridazinone

HRID 1946448Notes

Reaction equation

HRID 1946448 reaction equation
[CH:1]([C:4]1[CH2:5][CH2:6][C:7](=[O:10])[NH:8][N:9]=1)([CH3:3])[CH3:2].BrBr>C(O)(=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:10])[NH:8][N:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 230280926-(Propan-2-yl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 230281476-Isopropyl-3-pyridazinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

4,5-Dihydro-6-isopropyl-3(2H)-pyridazinone (3.10 g) was dissolved in acetic acid (30.0 ml), and bromine (3.50 g, 22.0 mmol) was added dropwise to the solution over 10 minutes under heating at 100° C. with stirring. After the reaction solution was heated for 1 hour under reflux, the acetic acid was distilled away under reduced pressure, and water (100 ml) was added to the residues which were then extracted 5 times with ethyl acetate. The extracts were combined, dried over anhydrous magnesium sulfate and concentrated to give a crude product of 6-isopropyl-3(2H)-pyridazinone. The yield was 3.30 g.

Workup

  1. temperatureAfter the reaction solution was heated for 1 hour
  2. temperatureunder reflux
  3. distillationthe acetic acid was distilled away under reduced pressure, and water (100 ml)
  4. additionwas added to the residues which
  5. extractionwere then extracted 5 times with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9dea74bbfae743a8b5d6f9a064ed2eb3
Source dataset
uspto-grants-2013_03
Patent number
US08399381B2

Reaction notes

Loading…