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

HRID 1091808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091808
[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:34]=[C:35]([CH:38]=[C:39]([CH:41]=O)[CH:40]=1)[C:36]#[N:37].C(N(CC)CC)C.O.[NH2:51][NH2:52]>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]([CH2:41][C:39]1[CH:38]=[C:35]([CH:34]=[C:33]([F:32])[CH:40]=1)[C:36]#[N:37])=[N:52][NH:51][C:8]2=[O:31]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 447549173-Fluoro-5-formylbenzonitrileHCID 86633041(7-Chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide

Produkt 1

HCID 577918013-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-5-fluorobenzonitrileAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(7-chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide (101) (2.88 g, 6.71 mmol) and 3-fluoro-5-formylbenzonitrile (1.0 g, 6.71 mmol) were dissolved DCM (60 mL), to this was added triethylamine (1.215 mL, 8.72 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 (3.36 g, 67.06 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 yellow solid (1.260 g, 59.9% yield), which was used without further purification; 1H NMR (400.132 MHz, DMSO) δ 4.68 (2H, s), 7.49 (1H, d), 7.58 (1H, s), 7.68 (1H, d), 7.82 (1H, t), 7.99 (1H, dd), 8.34 (1H, dd), 12.82 (1H, s); m/z (LC-MS, ESI−), RT=2.21 (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-140c4d4c25c2402da9716be9fc007d82
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129380B2

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