Ammonia → 1-(3-Phenoxyanilino)-4-(4-pyridylmethyl)phthalazine

HRID 1384146

Reaction equation

HRID 1384146 reaction equation
Cl[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.[O:19]([C:26]1[CH:32]=[CH:31][C:29](N)=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH3:33]>ClCCl.CO>[O:19]([C:26]1[CH:32]=[C:31]([CH:29]=[CH:28][CH:27]=1)[NH:33][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)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8764(4-Aminophenoxy)benzeneHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 227420031-(3-Phenoxyanilino)-4-(4-pyridylmethyl)phthalazine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 256 mg (1.00 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine and 556 mg (3.00 mmol) 4-phenoxyaniline (Aldrich) is heated for 2 h at 90° C. The melt is cooled and stirred with 6 ml NH3 solution (10% in water: or 10 ml sat. NaHCO3 solution) and 15 ml dichloromethane/methanol 50:1 for 30 min. The aqueous phase is then separated off and extracted again with dichloromethane. The organic phase is dried (Na2SO4), concentrated by evaporation, and chromatographed (SiO2; ethyl acetate→ethyl acetate/CH3OH 19:1→10:1). Crystallization from acetonitrile yields the title compound: m.p.: 186-1 89° C.; Anal. calc. (C26H21N4O) C 77.02%, H 5.22%, N 13.82%; found C 77.2%, H 4.9%, N 13.8%.

Workup

  1. temperatureThe melt is cooled
  2. customThe aqueous phase is then separated off
  3. extractionextracted again with dichloromethane
  4. dry with materialThe organic phase is dried (Na2SO4)
  5. concentrationconcentrated by evaporation
  6. customchromatographed (SiO2; ethyl acetate→ethyl acetate/CH3OH 19:1→10:1)
  7. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-e4af79b0d7b34a93a608936e1f118b90
Source dataset
uspto-grants-2001_07
Patent number
US06258812B1

Linked notes

Loading…