Ethyl bromoacetate → 6-(4-carbethoxymethoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

HRID 344640Notes

Reaction equation

HRID 344640 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[C:23]([CH2:22][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1358275406-(4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 136876766-(4-carbethoxymethoxyphenyl)-4,5-dihydro-3(2H)-pyridazinoneYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.00 g (10.5 mmol) of the phenol prepared above, 1.60g (11.6 mmol) of anhydrous K2CO3, 1.304 ml (11.8 mmol) of ethyl bromoacetate, and 40 ml of DMF is heated at 100° C. for 2 hrs under N2. The DMF is removed under vacuum and the residue taken up in 150 ml of EtOAc and 75 ml of water. The organic phase is washed with 50 ml of 5% aqueous NaOH, twice with saturated NaCl, dried (MgSO4), filtered, and the solvent removed to leave 2.186 g of a slightly yellow solid. This is recrystallized from hexane-EtOAc to give 2.01 g of 6-(4-carboethoxymethoxyphenyl)-4,5-dihydro3(2H)-pyridazinone as a white, crystalline solid, m.p. 127°-129° C. Yield 69%.

Workup

  1. customThe DMF is removed under vacuum
  2. washThe organic phase is washed with 50 ml of 5% aqueous NaOH, twice with saturated NaCl
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed
  6. customto leave 2.186 g of a slightly yellow solid
  7. customThis is recrystallized from hexane-EtOAc

Sources & evidence

ORD record
ord-4badcf903e4749d0aef7134269c060fd
Source dataset
uspto-grants-1991_10
Patent number
US05053338

Reaction notes

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