Triethylamine → 3-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile

HRID 1091797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091797
[Br-].[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)O[C:8]2=[O:31].[CH:32]([C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[C:37]#[N:38])=O.C(N(CC)CC)C.O.[NH2:50][NH2:51]>CN(C=O)C.CCO.O.C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10]([CH2:32][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[C:37]#[N:38])=[N:51][NH:50][C:8]2=[O:31]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 90670m-FormylbenzonitrileHCID 86633041(7-Chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide

Produkt 1

HCID 577917833-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrileAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(7-chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide (101) (10 g, 23.26 mmol) and 3-formylbenzonitrile (3.20 g, 24.43 mmol) were dissolved DCM (60 mL), to this was added triethylamine (4.22 mL, 30.24 mmol) and the reaction was stirred overnight. The reaction mixture was filtered to afford a white solid. To this was added water (40 mL), EtOH (40 mL) and DMF (4 mL). Hydrazine hydrate (11.65 g, 232.64 mmol) was added and the reaction was heated at reflux overnight. The reaction was cooled and the precipitate was collected by filtration, washed with EtOH (25 mL) and air dried to afford the desired material as a white solid (3.75 g, 54.5% yield), which was used without further purification; 1H NMR (400.132 MHz, DMSO) δ 4.66 (2H, s), 7.53-7.47 (2H, m), 7.68-7.66 (2H, m), 7.81 (1H, t), 7.97 (1H, d), 8.33 (1H, d), 12.55 (1H, s); m/z (LC-MS, ESI−), RT=2.04 (M−H 294).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customto afford a white solid
  3. temperaturethe reaction was heated
  4. temperatureat reflux overnight
  5. temperatureThe reaction was cooled
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with EtOH (25 mL) and air
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6d1c81a291674fdd83a8c36320dfa5bd
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129380B2

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