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

HRID 49904

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

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.: 186-189° C.; Anal. calc. (C26H21N4O) C, 77.02%; H, 5.22%; N, 13.82%. found C, 77.2%; H, 4.9%; N, 13.8%. The starting material is prepared as follows:

Workup

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

Sources & evidence

ORD record: ord-2a80a385c8eb4860ba25661439f17251
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06710047B2

Linked notes

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