3-Aminophenol → 1-(3-Hydroxyanilino)-4-(4-pyridylmethyl)phthalazine

HRID 49868

Reaktionsgleichung

Reaktionsgleichung von HRID 49868
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[NH2:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1>C([O-])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>[OH:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[NH:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1

Komponenten

6

Edukt 2

HCID 115683-AminophenolHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Produkt 1

HCID 64193911-(3-Hydroxyanilino)-4-(4-pyridylmethyl)phthalazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 175AcetateLösungsmittelHCID 887MethanolLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 0.384 g (1.5 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine and 0.491 g (4.5 mmol) 3-aminophenol is heated under nitrogen atmosphere for 1 h at 90° C. and for 3 h at 120° C. The reaction mixture is then taken up in a mixture of 30 ml acetate and 20 ml 20% aqueous potassium carbonate solution while stirring for about 4 h, and the filtration material is digested for 20 min in 20 ml of boiling methanol. After cooling to RT, filtration, washing of the filter residue with methanol, and drying under HV (8 h, 130° C.), title compound is obtained with a water content of 1.94%; m.p. 217-219° C.; ESI-MS: (M+H)+=329.

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. filtrationfiltration
  3. washwashing of the filter residue with methanol
  4. customdrying under HV (8 h, 130° C.)

Quellen und Nachweise

ORD-Eintrag
ord-13dac9bc62b74569911d6cec94e6ece0
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710047B2

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