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

HRID 1590789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590789
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 136876936-[4-carboethoxypropyloxy-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinoneAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-81809baae0bc439e8b9aa391b6eda72b
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204463

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