Tert-Butyl nitrite → 3-Methyl-6-nitro-1H-indazole

HRID 645675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645675
[CH2:1]([C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5])[CH3:2].[N:13](OC(C)(C)C)=O>C(O)(=O)C>[CH3:2][C:1]1[C:3]2[C:4](=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=2)[NH:5][N:13]=1

Komponenten

4

Edukt 2

HCID 10906Tert-Butyl nitriteHCID 41554782-Ethyl-5-nitroaniline

Produkt 1

HCID 109210543-Methyl-6-nitro-1H-indazoleAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

To a mixture of 2-ethyl-5-nitroaniline (2 g, 12 mmol) in acetic acid (AcOH) (60 mL) at ambient temperature was added a solution of tert-butyl nitrite (t-BuONO) (1.8 mL, 12 mmol) in AcOH (8 mL). After stirring at ambient temperature for 1 h, AcOH was removed in vacuo. The resulting residue was dissolved in ethyl acetate (EtOAc), washed with Sat. NaHCO3, dried over Na2SO4, and concentrated to afford 3-methyl-6-nitroindazole (1.2 g).

Aufarbeitung

  1. customAcOH was removed in vacuo
  2. dissolutionThe resulting residue was dissolved in ethyl acetate (EtOAc)
  3. washwashed with Sat. NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d7327e836b284eada67b7622744f8390
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705004B2

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