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2-Bromoaniline → ethyl 7-bromo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate

HRID 2199710
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2199710
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].N([O-])=[O:10].[Na+].[C:13]([O-])(=O)[CH3:14].[Na+].[CH2:18]([O:20][C:21]([CH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28])=[O:22])[CH3:19]>Cl.O>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[NH:4][C:25]([C:24]([O:28][CH2:13][CH3:14])=[O:10])=[C:26]2[CH2:27][CH2:23][C:21]([O:20][CH2:18][CH3:19])=[O:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 119922-BromoanilineHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Produkt 1

HCID 68940416ethyl 7-bromo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313
Hydrochloric Acid
Lösungsmittel
HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
19 °C

Versuchsvorschrift

A mixture of 2-bromoaniline (34.2 g) in 5M HCl (50 mL) and water (250 mL) at 0° C. was treated with NaNO2 (13.8 g) in water (200 mL). After addition, sodium acetate (92.3 g) in water (250 mL) and 2-oxo-cyclopentanecarboxylic acid ethyl ester (30 mL) were added. The mixture was stirred for 15 minutes, warmed to 19° C. over two hours and extracted with dichloromethane. The extract was dried (MgSO4), filtered and concentrated. The concentrate was dissolved in 1.1:1 H2SO4:ethanol (30 mL), refluxed overnight, cooled to room temperature, quenched with water (1.5 L), and filtered. The filtrant was dissolved in dichloromethane (200 mL) and filtered through a Flash 75 cartridge with dichloromethane. After concentration, the product was recrystallized from hexane.

Aufarbeitung

  1. additionwere added
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe concentrate was dissolved in 1.1:1 H2SO4
  7. temperatureethanol (30 mL), refluxed overnight
  8. temperaturecooled to room temperature
  9. customquenched with water (1.5 L)
  10. filtrationfiltered
  11. dissolutionThe filtrant was dissolved in dichloromethane (200 mL)
  12. filtrationfiltered through a Flash 75 cartridge with dichloromethane
  13. concentrationAfter concentration
  14. customthe product was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-6502f330eecf471d84a49b8233d2caad
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09359296B2

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