2-Nitropropane → 3-(2,2-dimethyl-2-nitroethyl)-5-chloro-1H-indole

HRID 1648391

Reaktionsgleichung

Reaktionsgleichung von HRID 1648391
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11]N(C)C.[OH-].[Na+].[N+:17]([CH:20]([CH3:22])[CH3:21])([O-:19])=[O:18]>C(O)(=O)C>[CH3:21][C:20]([CH3:22])([N+:17]([O-:19])=[O:18])[CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[NH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 3982-NitropropaneHCID 14798Sodium HydroxideHCID 134914391-(5-Chloro-1H-indol-3-yl)-N,N-dimethylmethanamine

Produkt 1

HCID 199199343-(2,2-dimethyl-2-nitroethyl)-5-chloro-1H-indoleAusbeute 105,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

5-Chloro-3-(dimethylaminomethyl)-1H-indole (10.6 g, 50.5 mmol), prepared as in Example 2, Step (a) and powdered sodium hydroxide (3.0 g, 75.0 mmol) were combined in 2-nitropropane (80 mL, 890.8 mmol) and the mixture was stirred at 120° C. and under nitrogen for 20 hours. The mixture was cooled, acidified with 10% acetic acid (80 mL), stirred at room temperature for 1 hour, and then extracted into ether. The organic phase was separated, washed with water and then brine, dried over magnesium sulfate, and evaporated. Filtration of the residue through a short column of silica gel gave 3-(2,2-dimethyl-2-nitroethyl)-5-chloro-1H-indole (13.5 g, 53.1 mmol) as a yellow oil.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. stirringstirred at room temperature for 1 hour
  3. extractionextracted into ether
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialbrine, dried over magnesium sulfate
  7. customevaporated
  8. filtrationFiltration of the residue through a short column of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2102caf230604c98ac327e7a3f369b75
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05436264

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