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

HRID 1384133Notes

Reaction equation

HRID 1384133 reaction equation
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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
200 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1e62313afc3e418e8c7232f5031a5ced
Source dataset
uspto-grants-2001_07
Patent number
US06258812B1

Reaction notes

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