Dimethylformamide → 4-[2-[1-Oxo-1,2-dihydrophthalazin-2-yl]ethoxy]benzaldehyde

HRID 350004

Reaktionsgleichung

Reaktionsgleichung von HRID 350004
Br[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[C:13]1(=[O:23])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[N:15][NH:14]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:23]=[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[N:15][N:14]1[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 83941(2H)-PhthalazinoneHCID 11430Potassium CarbonateHCID 2627064-(2-Bromoethoxy)Benzaldehyde

Produkt 1

HCID 111409394-[2-[1-Oxo-1,2-dihydrophthalazin-2-yl]ethoxy]benzaldehydeAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-(2-bromoethoxy)benzaldehyde (4.97 g), 1(2H)-phthalazinone (3.27 g), potassium carbonate (6.20 g) and N,N-dimethylformamide (50 ml) was stirred at 80° C. for 5 hours. After cooling, the reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated to obtain 4-[2-[1-oxo-2(1H)-phthalazinyl]ethoxy]benzaldehyde (5.36 g, yield 84%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 126–127° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-59c7c15139584e55bf4a718d7b9e51ec
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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