Sodium Carbonate → 2-(tert-Butyl)-6-nitroindoline

HRID 73919

Reaktionsgleichung

Reaktionsgleichung von HRID 73919
[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1)([CH3:4])([CH3:3])[CH3:2].C(C1NC2C(C=1)=CC=CC=2)(C)(C)C.[N+:27]([O-])([O-:29])=[O:28].[K+].C([O-])([O-])=O.[Na+].[Na+]>OS(O)(=O)=O>[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:27]([O-:29])=[O:28])=[CH:10][CH:11]=2)[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 5941662-tert-Butyl-1H-indoleHCID 46426432-(tert-Butyl)indoline

Produkt 1

HCID 574701952-(tert-Butyl)-6-nitroindolineAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a solution of the mixture of 2-tert-butyl-2,3-dihydro-1H-indole and 2-tert-butyl-1H-indole (9.7 g) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 55.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h, carefully poured into cracked ice, basified with Na2CO3 to pH-8 and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (4.0 g, 32% over 2 steps).

Aufarbeitung

  1. customat 0° C
  2. additioncarefully poured into cracked ice
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d209ee55a7144c0491fdf3d3288c2560
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829204B2

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