4-Aminobiphenyl → N-(4-phenylphenyl)-4-(pyridin-4-ylmethyl)phthalazin-1-amine

HRID 1057709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057709
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Cl.C(N(CC)CC)C.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:26][CH:25]=1.[N:36]1[CH:41]=[CH:40][C:39]([CH2:42][C:43]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46](=O)[NH:45][N:44]=2)=[CH:38][CH:37]=1.C(=O)([O-])[O-]>O.ClCCl.CO>[C:30]1([C:27]2[CH:26]=[CH:25][C:24]([NH:23][C:46]3[C:47]4[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=4)[C:43]([CH2:42][C:39]4[CH:40]=[CH:41][N:36]=[CH:37][CH:38]=4)=[N:44][N:45]=3)=[CH:29][CH:28]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

8

Edukt 5

HCID 71024-AminobiphenylHCID 11130Triethylamine hydrochlorideHCID 14812Phosphorus oxide (P4O10)HCID 19660Carbonate IonHCID 7899544-(4-Pyridylmethyl)-1(2H)-phtalazinone

Produkt 1

HCID 6419389N-(4-phenylphenyl)-4-(pyridin-4-ylmethyl)phthalazin-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 2.41 g (16.98 mmol) phosphorus pentoxide, 2.32 g (16.85 mmol) triethylamine hydrochloride, 3 g (17.73 mmol) 4-aminobiphenyl, and 1 g (4.21 mmol) 4-(4-pyridylmethyl)-1(2H)-phthalazinone is stirred for 20 h at 200° C. under a nitrogen atmosphere. After cooling to RT, the hyalinocrystalline melt is distributed between a dichloromethane/methanol mixture (99:1) and a mixture of water and saturated aqueous carbonate solution (1:1) with intensive stirring and the use of an ultrasonic bath. The organic phase dried over sodium sulfate is evaporated under vacuum and the residue purified by means of flash chromatography on silica gel with particle size 0.04-0.06 mm, using a dichloromethane/methanol mixture (49:1). Title compound is obtained after evaporation of the product-containing fractions under vacuum and recrystallization of the residue from acetonitrile; m.p. 189-191° C.; ESI-MS: (M+H)+=389.

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. stirringwith intensive stirring
  3. dry with materialThe organic phase dried over sodium sulfate
  4. customis evaporated under vacuum
  5. customthe residue purified by means of flash chromatography on silica gel with particle size 0.04-0.06 mm

Quellen und Nachweise

ORD-Eintrag
ord-383323b6e4fb4916aaabfa63371d3f2f
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514974B2

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