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Hydrazine → 4-(4-methoxybenzyl)phthalazin-1(2H)-one

HRID 911119
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 911119
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([NH:16]C)=[O:15])=O)=[CH:5][CH:4]=1.[NH2:22]N>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:12]3[C:13](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14](=[O:15])[NH:16][N:22]=2)=[CH:5][CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 667315312-(2-(4-methoxyphenyl)acetyl)-N-methylbenzamide

Produkt 1

HCID 123328504-(4-methoxybenzyl)phthalazin-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 2-(2-(4-methoxyphenyl)acetyl)-N-methylbenzamide (1.76 g, 6.20 mmol) in EtOH (20 mL) was added hydrazine (3.50 ml, 112 mmol). A water condenser was attached and the mixture was heated to reflux under a nitrogen atmosphere for 5 days. After concentration, the reaction was diluted with EtOAc and extracted with water. The organics were dried over sodium sulfate, filtered and concentrated. The crude was purified by washing the resulting solid with diethyl ether and filtering to yield 4-(4-methoxybenzyl)phthalazin-1(2H)-one as a white solid. MS m/z=267[M+1]+. Calc'd for C16H14N2O2: 266.30.

Aufarbeitung

  1. customA water condenser was attached
  2. temperaturethe mixture was heated
  3. temperatureto reflux under a nitrogen atmosphere for 5 days
  4. concentrationAfter concentration
  5. additionthe reaction was diluted with EtOAc
  6. extractionextracted with water
  7. dry with materialThe organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude was purified
  11. washby washing the resulting solid with diethyl ether
  12. filtrationfiltering

Quellen und Nachweise

ORD-Eintrag
ord-6a761fe7acb74137adaf295429d748d9
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08022221B2

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