2-Nitropropane → 3-(2-Methyl-2-nitropropyl)-7-(benzyloxy)indole

HRID 1272208

Reaktionsgleichung

Reaktionsgleichung von HRID 1272208
CN([CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8]=2[NH:7][CH:6]=1)C.[OH-].[Na+].[N+:24]([CH:27]([CH3:29])[CH3:28])([O-:26])=[O:25]>CCOCC>[CH3:28][C:27]([N+:24]([O-:26])=[O:25])([CH3:29])[CH2:4][C:5]1[C:9]2[C:8](=[C:13]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:12]=[CH:11][CH:10]=2)[NH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 3982-Nitropropane2×HCID 14798Sodium HydroxideHCID 2608077-Benzyloxygramine

Produkt 1

HCID 220147783-(2-Methyl-2-nitropropyl)-7-(benzyloxy)indoleAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 7-benzyloxy gramine (1.99 g, 7.10 mmol), solid NaOH (298 mg, 7.22 mmol) and 2-nitropropane (4.5 mL, 50 mmol) is heated to reflux. After 10 minutes at reflux, a thick slurry developed which is difficult to stir. Gas evolution is observed, and an additional 1 mL of 2-nitropropane is added to loosen the mixture. After 29 hours, the mixture is allowed to cool to ambient temperature. Ether (30 mL) is added and the mixture is filtered. The filtrate is treated with 10% acetic acid (6 mL), the layers are separated and the organic layer is rinsed with water (2×25 mL). The organic layer is dried (Na2SO4) and concentrated to give 2.12 g of 3-(2-methyl-2-nitropropyl)-7-(benzyloxy)indole (92%). MS (ES+) m/z 325.

Aufarbeitung

  1. temperatureis heated to reflux
  2. temperatureAfter 10 minutes at reflux
  3. filtrationthe mixture is filtered
  4. additionThe filtrate is treated with 10% acetic acid (6 mL)
  5. customthe layers are separated
  6. washthe organic layer is rinsed with water (2×25 mL)
  7. dry with materialThe organic layer is dried (Na2SO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-49a35df9e60d4d9fabde5fc1b0560cc3
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208505B2

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