Hydrochloric Acid → 1-Benzyl-5-nitro-1,2-dihydro-3h-indazol-3-one

HRID 490551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490551
F[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH:45]1[CH:50]=[CH:49][C:48]([CH2:51][NH:52][NH2:53])=[CH:47][CH:46]=1.Cl.Cl.Cl>CN(C=O)C>[CH2:51]([N:52]1[C:2]2[C:3](=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)[C:4](=[O:6])[NH:53]1)[C:48]1[CH:49]=[CH:50][CH:45]=[CH:46][CH:47]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 146540Benzylhydrazine dihydrochlorideHCID 2809972-Fluoro-5-nitrobenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 3849951-Benzyl-5-nitro-1,2-dihydro-3h-indazol-3-oneAusbeute 35,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-fluoro-5-nitrobenzoic acid (0.5 g) in DMF (9 mL) was added TBTU (1.04 g) followed by N-ethyldiisopropylamine (2.3 mL). After 10 minutes benzylhydrazine.2HCl (0.63 g) was added. The reaction mixture was stirred at ambient temperature for 22 hours and the reaction was poured onto aqueous 1N HCl solution and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo. Purification via ISCO combiflash chromatography afforded pure desired 1-benzyl-5-nitro-1,2-dihydro-indazol-3-one (0.26 g) as a yellow solid. MS (ESI−):268.3 ([M−H]−).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification via ISCO combiflash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c29723ba24224e10a59bfe12c3fb473a
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528158B2

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