1-Chloro-4-(4-pyridinylmethyl)phthalazine → 1-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine hydrochloride

HRID 49858

Reaktionsgleichung

Reaktionsgleichung von HRID 49858
[Cl:1][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.Cl.[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>C(O)C>[ClH:1].[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazineHCID 52843634-Chloroaniline hydrochloride

Produkt 1

HCID 98862921-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 0.972 g (3.8 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine, 0.656 g (4 mmol) 4-chloroaniline hydrochloride (Research Organics, Inc., Cleveland, Ohio, USA) and 20 ml ethanol is heated for 2 h under reflux. The reaction mixture is cooled in an ice bath, filtered, and the crystallizate washed with a little ethanol and ether. After drying under HV for 8 h at 110° C. and for 10 h at 150° C., the title compound is obtained as a result of thermal removal of HCl; m.p. >270° C.; 1H NMR (DMSO-d6) 9.80-11.40 (br), 8.89-8.94 (m, 1H), 8.67 (d, 2H), 8.25-8.30 (m, 1H), 8.06-8.17 (m, 2H), 7.87 (d, 2H), 7.69 (d, 2H), 7.49 (d, 2H), 4.81 (s, 2H); ESI-MS: (M+H)+=347.

Aufarbeitung

  1. temperatureis heated for 2 h
  2. temperatureunder reflux
  3. temperatureThe reaction mixture is cooled in an ice bath
  4. filtrationfiltered
  5. washthe crystallizate washed with a little ethanol and ether
  6. customAfter drying under HV for 8 h at 110° C. and for 10 h at 150° C.

Quellen und Nachweise

ORD-Eintrag
ord-cdb63b9725784fcf99133e81a8c8bde5
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710047B2

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