Potassium Carbonate → 6-[4-carboethoxypropyloxy-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 1590789Notes

Reaction equation

HRID 1590789 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:10][CH2:11][C:12](=[O:15])[NH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C>[C:26]([CH2:25][CH2:24][CH2:23][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH2:10][CH2:11][C:12](=[O:15])[NH:13][N:14]=2)=[CH:3][C:2]=1[Cl:1])([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 1355888616-(3-chloro-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 136876936-[4-carboethoxypropyloxy-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinoneYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.500 mg (6.675 mmol) of 6-(3-chloro-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone, prepared by the method of Eur. Pat. Appl. 178,189, 1.010 g (7.34 mmol) K2CO3, and 1.463 g (7.50 mmol) of ethyl 4-bromobutyrate in 30 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 50 ml of water. The organic phase is washed with 50 ml of 5% NaOH, then saturated NaCl solution, dried (MgSO4), and the solvent removed to leave a white solid. This solid is recrystallized from hexane-EtoAc to give 1.711 g of 6-[4-carboethoxypropyloxy-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone as white needles, m.p. 109°-110° C. Yield, 82%.

Workup

  1. customprepared by the method of Eur
  2. customThe DMF is removed under vacuum
  3. washThe organic phase is washed with 50 ml of 5% NaOH
  4. dry with materialsaturated NaCl solution, dried (MgSO4)
  5. customthe solvent removed
  6. customto leave a white solid
  7. customThis solid is recrystallized from hexane-EtoAc

Sources & evidence

ORD record
ord-81809baae0bc439e8b9aa391b6eda72b
Source dataset
uspto-grants-1993_04
Patent number
US05204463

Reaction notes

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