Dimethylformamide → N-(4-Chlorophenyl)-4-[(pyridin-4-yl)methoxy]phthalazin-1-amine

HRID 49888

Reaktionsgleichung

Reaktionsgleichung von HRID 49888
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[H-].[Na+].CN(C=O)C.Cl.Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[N:20][N:19]=1>O>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([NH:28][C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]([O:1][CH2:2][C:3]3[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=3)=[N:19][N:20]=2)=[CH:34][CH:33]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 114724-HydroxymethylpyridineHCID 24758Sodium hydrideHCID 223972781-Chloro-4-(4-chloroanilino)phthalazine hydrochloride

Produkt 1

HCID 22397275N-(4-Chlorophenyl)-4-[(pyridin-4-yl)methoxy]phthalazin-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1 g (9.16 mmol) 4-hydroxymethylpyridine, 0.44 g (11.0 mmol) sodium hydride (60% dispersion in oil) and 15 ml DMF is incubated for 20 min at 0° C. while stirring in a nitrogen atmosphere. At RT, 1 g (3.07 mmol) 1-chloro-4-(4-chloroanilino)phthalazine hydrochloride is added to the mixture, which is stirred for about 1 h at 50° C. and for 15 h at 80° C. Addition to the reaction mixture of a little water, evaporation under vacuum, recrystallization of the residue from methanol, and drying under HV yield the title compound with a water content of 3.36%; m.p. 139-141° C.; ESI-MS: (M+H)+=363.

Aufarbeitung

  1. stirringis stirred for about 1 h at 50° C. and for 15 h at 80° C
  2. additionAddition
  3. customunder vacuum, recrystallization of the residue from methanol
  4. customdrying under HV

Quellen und Nachweise

ORD-Eintrag
ord-256c130ffb2246fca5849c7cc5eea85e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710047B2

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