Acetic Acid → 4-fluoro-3-(2-methyl-2-nitropropyl)-1H-indole

HRID 8121

Reaktionsgleichung

Reaktionsgleichung von HRID 8121
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](CCN(C)C)=[CH:5][NH:6]2.[OH-].[Na+].[C:18](O)(=O)C.[N+:22]([CH:25]([CH3:27])[CH3:26])([O-:24])=[O:23]>C(OCC)(=O)C.[Cl-].[Na+].O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:26][C:25]([CH3:18])([N+:22]([O-:24])=[O:23])[CH3:27])=[CH:5][NH:6]2

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 3982-NitropropaneHCID 14798Sodium HydroxideHCID 114921621644-64-0

Produkt 1

HCID 220148134-fluoro-3-(2-methyl-2-nitropropyl)-1H-indoleAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A slurry of 4-fluoro-3-(dimethylaminoethyl)-1H-indole (4.3 g, 22.4 mmol) in 14.1 ml of 2-nitropropane is treated with solid NaOH (941 mg, 23.5 mmol), and the resulting mixture is heated at reflux overnight. After cooling to ambient temperature, the reaction mixture is acidified with 10%. aqueous acetic acid (25 ml) and stirring is continued for 30 minutes. The reaction mixture is diluted with ethyl acetate (50 ml) and brine (50 ml). The layers are separated, and the organic layer is washed with brine (50 ml), dried over Na2SO4 and concentrated in vacuo to give 3.71 g of 4-fluoro-3-(2-methyl-2-nitropropyl)-1H-indole (76%).

Aufarbeitung

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux overnight
  3. customThe layers are separated
  4. washthe organic layer is washed with brine (50 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a38914c6c46e4909b2e3f31bcb03efa9
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087635B2

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