4-Aminophenol → 4-((4-Phenylphthalazin-1-yl)amino)phenol

HRID 593974

Reaktionsgleichung

Reaktionsgleichung von HRID 593974
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][N:11]=1>C1C=CC=CC=1>[C:20]1([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=3)=[N:11][N:12]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

4

Edukt 2

HCID 4034-AminophenolHCID 2721091-Chloro-4-phenylphthalazine

Produkt 1

HCID 28691684-((4-Phenylphthalazin-1-yl)amino)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A pressure bottle was charged with 4-aminophenol (0.453 g, 0.416 mmol), 1-chloro-4-phenylphthalazine (1.00 g, 0.416 mmol) and 16.8 mL of benzene. The bottle was sealed and heated to 100° C. for 25 h. The reaction mixture was concentrated. The crude material was dissolved in methanol and was purified by Gilson reverse phase liquid chromatography, 5-75% ACN/H2O/0.1% TFA over 14 min. The product-containing fractions were combined, brought to basic pH by addition of 1M NaHCO3, and extracted with dichloromethane. The organic portion was dried with MgSO4, filtered and concentrated to provide 4-(4-phenylphthalazin-1-ylamino)phenol as a yellow solid. MS m/z=314 [M+H]+. Calc'd for C20H15N3O: 313.35.

Aufarbeitung

  1. customThe bottle was sealed
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionThe crude material was dissolved in methanol
  4. customwas purified by Gilson reverse phase liquid chromatography, 5-75% ACN/H2O/0.1% TFA over 14 min
  5. additionbrought to basic pH by addition of 1M NaHCO3
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic portion was dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a6b1e1ef074f458a8308fbebfeee4f42
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242961B2

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