Triethylamine → 5-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-2-fluorobenzonitrile

HRID 1091782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091782
[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].[F:32][C:33]1[CH:40]=[CH:39][C:38]([CH:41]=O)=[CH:37][C:34]=1[C:35]#[N:36].C(N(CC)CC)C.O.[NH2:51][NH2:52]>C(Cl)Cl.CN(C=O)C.CCO.O>[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10]([CH2:41][C:38]1[CH:39]=[CH:40][C:33]([F:32])=[C:34]([CH:37]=1)[C:35]#[N:36])=[N:52][NH:51][C:8]2=[O:31]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 27695822-Fluoro-5-formylbenzonitrileHCID 86633041(7-Chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide

Produkt 1

HCID 577918005-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-2-fluorobenzonitrileAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(7-chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide (101) (9.3 g, 21.64 mmol) and 2-fluoro-5-formylbenzonitrile (3.55 g, 23.80 mmol) were dissolved in DCM (60 mL), to this was added triethylamine (3.92 mL, 28.13 mmol) and the reaction was stirred overnight. The reaction mixture was evaporated to afford a brown solid. To this was added water (40 mL), EtOH (40 mL) and DMF (4 mL). Hydrazine hydrate (10.83 g, 216.35 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 compound as a yellow solid (6.10 g, 90%), which was used without further purification; 1H NMR (400.132 MHz, DMSO) δ 4.64 (2H, s), 7.44 (1H, t), 7.63-7.59 (1H, m), 7.78 (1H, dd), 7.81 (1H, t), 7.98 (1H, dd), 8.33 (1H, dd); m/z (LC-MS, ESI+), RT=2.17 (M−H 312).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customto afford a brown 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-b7007d6824c54f59b0065e0185702814
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129380B2

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