3-Chloro-4-fluoroaniline → 1-(3-Chloro-4-fluoroanilino)-4-(4-pyridylmethyl)phthalazine

HRID 49884

Reaktionsgleichung

Reaktionsgleichung von HRID 49884
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Cl.C(N(CC)CC)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[F:31])[NH2:27].[N:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42](=O)[NH:41][N:40]=2)=[CH:34][CH:33]=1.[OH-].[Na+]>O.ClCCl>[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[F:31])[NH:27][C:42]1[C:43]2[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:39]([CH2:38][C:35]2[CH:36]=[CH:37][N:32]=[CH:33][CH:34]=2)=[N:40][N:41]=1

Komponenten

8

Edukt 5

HCID 97083-Chloro-4-fluoroanilineHCID 11130Triethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 7899544-(4-Pyridylmethyl)-1(2H)-phtalazinone

Produkt 1

HCID 97991931-(3-Chloro-4-fluoroanilino)-4-(4-pyridylmethyl)phthalazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 1.42 g (10 mmol) phosphorus pentoxide, 1.38 g (10 mmol) triethylamine hydrochloride, and 1.46 g (10 mmol) 3-chloro-4-fluoroaniline is heated and stirred in a nitrogen atmosphere at 200° C. until a homogeneous melt has formed. To the melt, 0.593 g (2.5 mmol) 4-(4-pyridylmethyl)-1(2H)-phthalazinone is added and the reaction mixture stirred for a further 3 h at 200° C. After cooling to RT, the hyalinocrystalline reaction mixture is distributed between 150 ml dichloromethane and a mixture of 10 ml water and 20 ml 2N sodium hydroxide solution with intensive stirring and sonication. The organic phase washed with water and dried over sodium sulfate is concentrated by evaporation and the residue recrystallized from acetate. Title compound is obtained after a second recrystallization from methanol/water and drying under HV (8 h at 100° C.); m.p. 185-187° C.; ESI-MS: (M+H)+=365.

Aufarbeitung

  1. temperatureis heated
  2. customhas formed
  3. stirringthe reaction mixture stirred for a further 3 h at 200° C
  4. temperatureAfter cooling to RT
  5. customthe hyalinocrystalline reaction mixture
  6. stirringwith intensive stirring
  7. customsonication
  8. washThe organic phase washed with water
  9. dry with materialdried over sodium sulfate
  10. concentrationis concentrated by evaporation
  11. customthe residue recrystallized from acetate

Quellen und Nachweise

ORD-Eintrag
ord-8dbc3bce22d84d228a83e727e949ad00
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710047B2

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