Ethyl bromoacetate → Ethyl 2-(4,5-dibromo-6-oxopyridazin-1(6H)-yl)acetate

HRID 2092068Notes

Reaction equation

HRID 2092068 reaction equation
[Br:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1[Br:8].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Br:8][C:7]1[CH:6]=[N:5][N:4]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3](=[O:9])[C:2]=1[Br:1]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2361814,5-Dibromo-2,3-dihydropyridazin-3-one

Product 1

HCID 59574424Ethyl 2-(4,5-dibromo-6-oxopyridazin-1(6H)-yl)acetateYield 110.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,5-Dibromopyridazin-3(2H)-one (5.0 g, 19.7 mmol) in N,N-dimethylformamide (50 mL) was stirred with ethyl bromoacetate (3.28 g, 29.5 mmol) and potassium carbonate (4.08 g, 29.5 mmol) at 80° C. for 1 hour and 40 minutes. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride three times and with saturated aqueous sodium chloride once, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give the desired product (7.42 g, 100% yield).

Workup

  1. additionwas added
  2. washthe organic layer was washed with saturated aqueous ammonium chloride three times and with saturated aqueous sodium chloride once
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a64f382498134737aba380d7eb795aba
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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