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

HRID 1384146

반응식

HRID 1384146 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

반응 조건

온도
90 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-e4af79b0d7b34a93a608936e1f118b90
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06258812B1

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