Potassium Carbonate → 6-[4-(3-phthalimidopropyloxy)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

HRID 344638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 344638
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:15])[N:12](C)[N:13]=2)=[CH:4][CH:3]=1.[C:16]([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25][N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36]>CN(C=O)C>[C:30]1(=[O:31])[N:26]([CH2:25][CH2:24][CH2:23][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]([CH3:16])[CH2:10][C:11](=[O:15])[NH:12][N:13]=3)=[CH:4][CH:3]=2)[C:27](=[O:36])[C:28]2=[CH:35][CH:34]=[CH:33][CH:32]=[C:29]12

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 1363382306-(4-hydroxyphenyl)-methyl-4,5-dihydro-3(2H)-pyridazinone

Produkt 1

HCID 150163386-[4-(3-phthalimidopropyloxy)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinoneAusbeute 104 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 500 mg (2.45 mmol) of 6-(4-hydroxyphenyl)-methyl-4,5-dihydro-3(2H)-pyridazinone (prepared by the method described in Eur. Pat. Appl. EP 178,189 A2), 373 mg (2.70 mmol) of powdered anhydrous K2CO3, and 790 mg (2.95 mmol) of N-(3-bromopropyl)phthalimide in 10 ml of DMF is heated at 100° C. for 2 hrs. The DMF is removed under vacuum, the residue is taken up in 125 ml of EtOAc and 100 ml of water, the organic phase washed once with 75 ml of water, died (MgSO4), and the solvent removed to give 0.997 g of 6-[4-(3-phthalimidopropyloxy)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone as a white solid. Yield, 99%.

Aufarbeitung

  1. customprepared by the method
  2. customThe DMF is removed under vacuum
  3. wash100 ml of water, the organic phase washed once with 75 ml of water
  4. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-8eede301b9d84d149ed6d042c0e5021e
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053338

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