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

HRID 49904

反応式

HRID 49904 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
90 °C

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-2a80a385c8eb4860ba25661439f17251
出典データセット
uspto-grants-2004_03
特許番号
US06710047B2

関連ノート

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